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  • 301.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ullah, Farman
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic asymmetric transformation (DYKAT) by combination of amine and transition metal cascade catalysis2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 302.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic asymmetric aziridination of α,β-unsaturated aldehydes2011In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 28, p. 7904-7917Article in journal (Refereed)
    Abstract [en]

    The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziridines with up to >19:1 d.r. and 99% ee. The aminocatalytic aziridination of α-monosubstituted enals gives access to terminal α-substituted-α-formyl aziridines in high yields and upto 99% ee. In the case of the organocatalytic aziridination of disubstituted α,β-unsaturated aldehydes, the transformations were highly diastereo- and enantioselective and give nearly enantiomerically pure β-formyl-functionalized aziridine products (99% ee). A highly enantioselective one-pot cascade sequence based on the combination of asymmetric amine and N-heterocycliccarbene catalysis (AHCC) is also disclosed. This one-pot three-component co-catalytic transformation between α,β-unsaturated aldehydes, hydroxylamine derivatives, and alcohols gives the corresponding N-tert-butoxycarbonyl and N-carbobenzyloxy-protected β-amino acid esters with ee values ranging from 92–99%. The mechanisms and stereochemistry of all these catalytic transformations are also discussed.

  • 303.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ghisu, Lorenza
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Bacsik, Zoltan
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid-Sweden University, Sweden.
    Enantioselective Heterogeneous Synergistic Catalysis for Asymmetric Cascade Transformations2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 11-12, p. 2485-2492Article in journal (Refereed)
    Abstract [en]

    A modular design for a novel heterogeneous synergistic catalytic system, which simultaneously activates the electrophile and nucleophile by the combined activation modes of a separate metal and non-metal catalyst, for asymmetric cascade transformations on a solid surface is disclosed. This modular catalysis strategy generates carbocycles (up to 97.5: 2.5 er) as well as spirocyclic oxindoles (97.5: 2.5 to > 99: 0.5 er), containing all-carbon quaternary centers, in a highly enantioselective fashion via a one-pot dynamic relay process.

  • 304.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ghisu, Lorenza
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cordova, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Zhang, Renyun
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mittuniversitetet, Sundsvall.
    Efficient and Highly Enantioselective Aerobic Oxidation-Michael-Carbocyclization Cascade Transformations by Integrated Pd(0)-CPG Nanoparticle/Chiral Amine Relay Catalysis2014In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 46, no 10, p. 1303-1310Article in journal (Refereed)
    Abstract [en]

    A series of highly diastereo- and enantioselective aerobic oxidation-Michael-carbocyclization cascade transformations by integrated heterogeneous Pd(0)-CPG nanoparticle/chiral amine relay catalysis are disclosed. The heterogeneous Pd(0)-CPG nanoparticle catalysts were efficient for both the sequential aerobic oxidation and dynamic kinetic asymmetric Michael-carbocyclization transformations, resulting in 1) oxidation of a variety of allylic alcohols to enals and 2) formation of cyclopentenes containing an all-carbon quaternary stereocenter in good to high yields with up to 20:1 dr and 99.5:0.5 er.

  • 305.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jiang, Yan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palo-Nieto, Carlos
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Incerti-Pradillos, Celia A.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tai, Cheuk-Wai
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Combined Heterogeneous Metal/Chiral Amine: Multiple Relay Catalysis for Versatile Eco-Friendly Synthesis2014In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 53, no 13, p. 3447-3451Article in journal (Refereed)
    Abstract [en]

    Herein is described a versatile and broad synergistic strategy for expansion of chemical space and the synthesis of valuable molecules (e.g. carbocycles and heterocycles), with up to three quaternary stereocenters, in a highly enantioselective fashion from simple alcohols (31examples, 95:5 to >99.5:0.5 e.r.) using integrated heterogeneous metal/chiral amine multiple relay catalysis and air/O-2 as the terminal oxidant. A novel highly 1,4-selective heterogeneous metal/amine co-catalyzed hydrogenation of enals was also added to the relay catalysis sequences.

  • 306.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzik, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    One-pot highly enantioselective catalytic Mannich-type reactions between aldehydes and stable α-amido sulfones: asymmetric synthesis of β-amino aldehydes and β-amino acids2010In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 51, no 2, p. 234-237Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective catalytic route to carbamate- and benzoate-protected beta-amino aldehydes and beta-amino acids is presented. The amino acid-catalyzed one-pot asymmetric reaction between unmodified aldehydes and alpha-amido sulfones gives the corresponding beta-amino compounds with up to 95:5 dr and 97-99%

  • 307.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Leijonmarck, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lehmann, Christian
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Lehmann, Christian W.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University.
    Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives2012In: ChemistryOpen, ISSN 2191-1363, Vol. 1, no 3, p. 134-139Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective, metal-free cascade reaction between di-1,2-N-protected hydrazine and α,β-unsaturated aldehydes is disclosed. The catalytic, asymmetric cascade transformation is a direct entry to 3-hydroxypyrazolidine and 3-allylpyrazolidine derivatives in one step and two steps, respectively, with >19:1 d.r. and 98–99 % ee using simple chiral pyrrolidines as catalysts.

  • 308.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhang, Qiong
    Leijonmarck, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Organocatalytic enantioselective aziridination of α-substituted α,β-unsaturated aldehydes: asymmetric synthesis ot terminal aziridines2010In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 352, no 18, p. 3201-3207Article in journal (Refereed)
    Abstract [en]

    The first example of a highly enantioselective organocatalytic aziridination of α-substituted α,β-unsaturated aldehydes is presented. The reaction is catalyzed by simple chiral amines and gives access to highly functional terminal azirdines containing an α-tertiary amine stereocenter in high yields and enantiomeric ratios (95.5:4.5–98:2).

  • 309.
    Deng, Hong-Ping
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Allylic sp (3) C-H borylation of alkenes via allyl-Pd intermediates: an efficient route to allylboronates2014In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, no 65, p. 9207-9210Article in journal (Refereed)
    Abstract [en]

    Palladium catalyzed allylic C-H functionalization was performed using exocyclic alkene substrates. Multi-component synthesis of stereodefined homoallylic alcohols could be performed using a reaction sequence involving allylic C-H borylation and allylation of aldehydes.

  • 310.
    Deng, Hong-Ping
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wang, Dong
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct Allylation of Quinones with Allylboronates2015In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 80, no 6, p. 3343-3348Article in journal (Refereed)
    Abstract [en]

    Allylboronates undergo C-H allylation of unsubstituted or monosubstituted benzoquinone and naphthoquinone substrates. In the case of 2,5- or 2,6-disubstituted quinones addition involving the substituted carbon takes place. Allylation with stereodefined allylboronates occurs with retention of the configuration.

  • 311.
    Deng, Youqian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartholomeyzik, Teresa
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Arylating Carbocyclization of Allenynes2012In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 51, no 11, p. 2703-2707Article in journal (Refereed)
  • 312.
    Deng, Youqian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Acyloxylation/Carbocyclization of Allenynes2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 11, p. 3217-3221Article in journal (Refereed)
  • 313.
    Deng, Youqian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Persson, Andreas K. A.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palladium-Catalyzed Oxidative Carbocyclizations2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 37, p. 11498-11523Article, review/survey (Refereed)
    Abstract [en]

    Palladium-catalyzed oxidative carboncarbon bond-forming annulations, that is, carbocyclization reactions, have recently emerged as efficient and atom-economical routes to carbo- and heterocycles, whereby less functionalized substrates and fewer synthetic steps are needed to obtain a target molecule compared with traditional non-oxidative carboncarbon bond-forming reactions. In this review, the synthetic efforts in palladium-catalyzed oxidative carbocyclization reactions are summarized.

  • 314.
    Deng, Youqian
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Teresa, Bartholomeyzik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Control of Selectivity in Palladium-Catalyzed Oxidative Carbocyclization/Borylation of Allenynes2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 24, p. 6283-6287Article in journal (Refereed)
    Abstract [en]

    In control: A highly selective carbocyclization/borylation of allenynes with bis(pinacolato)diboron (B2pin2) under palladium catalysis and with p-benzoquinone (BQ) as the oxidant was developed. The use of either LiOAc⋅2 H2O with 1,2-dichloroethane (DCE) as the solvent or BF3⋅Et2O together with THF is crucial for the selective formation of borylated trienes and vinylallenes, respectively.

  • 315.
    Deska, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enzymatic kinetic resolution of primary allenic alcohols. Application to the total synthesis and stereochemical assignment of striatisporolide A2009In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 7, no 17, p. 3379-3381Article in journal (Refereed)
  • 316.
    Deska, Jan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    del Pozo Ochoa, Carolina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Chemoenzymatic dynamic kinetic resolution of axially chiral allenes2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 15, p. 4447-4451Article in journal (Refereed)
    Abstract [en]

    Dimeric palladium bromide complexes bearing monodentate N-heterocyclic carbene ligands have been identified as efficient catalysts for the chemoselective racemization of axially chiral allenyl alcohols. In combination with porcine pancreatic lipase as biocatalyst, a dynamic kinetic resolution has been developed, giving access to optically active allenes in good yield and high enantiomeric purity (

  • 317.
    Dey, Chandan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lindstedt, Erik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Wallenberg Research Centre at Stellenbosch University, South Africa.
    Metal-Free C-Arylation of Nitro Compounds with Diaryliodonium Salts2015In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052, Vol. 17, no 18, p. 4554-4557Article in journal (Refereed)
    Abstract [en]

    An efficient, mild, and metal-free arylation of nitro-alkanes with diaryliodonium salts has been developed, giving easy access to tertiary nitro compounds. The reaction proceeds in high yields without the need for excess reagents and can be extended to alpha-arylation of nitroesters. Nitroalkanes were selectively C-arylated in the presence of other easily arylated functional groups, such as phenols and aliphatic alcohols.

  • 318.
    Di Francesco, Davide
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Subbotina, Elena
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rautiainen, Sari
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Samec, Joseph S. M.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ductile Pd-Catalysed Hydrodearomatization of Phenol-Containing Bio-Oils Into Either Ketones or Alcohols using PMHS and H2O as Hydrogen Source2018In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, no 20, p. 3924-3929Article in journal (Refereed)
    Abstract [en]

    A series of phenolic bio-oil components were selectively hydrodearomatized by palladium on carbon into the corresponding ketones or alcohols in excellent yields using polymethylhydrosiloxane and water as reducing agent. The selectivity of the reaction was governed by the water concentration where selectivity to alcohol was favoured at higher water concentrations. As phenolic bio-oil examples cardanol and beech wood tar creosote were studied as substrate to the developed reaction conditions. Cardanol was hydrodearomatized into 3-pentadecylcyclohexanone in excellent yield. From beech wood tar creosote, a mixture of cyclohexanols was produced. No hydrodeoxygenation occurred, suggesting the applicability of the reported method for the production of ketone-alcohol oil from biomass.

  • 319.
    Diner, Colin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Recent Advances in the Preparation and Application of Allylboron Species in Organic Synthesis2017In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 139, no 1, p. 2-14Article, review/survey (Refereed)
    Abstract [en]

    In this Perspective we will highlight the most important recent breakthroughs in selective allylboron chemistry (both the synthesis and application of these species). In addition we will provide an outlook toward the future of this promising subfield of organic synthesis.

  • 320. Dorange, Ismet
    et al.
    Löfstedt, Joakim
    Franzén, Johan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Närhi, Katja
    Bäckvall, Jan E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Allenes as Carbon Nucleophiles in Intramolecular Attack on (π-1,3-diene)Palladium Complexes: Evidence for trans-Carbopalladation of the 1,3-Diene2003In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 9, no 14, p. 3445-3449Article in journal (Refereed)
  • 321. Dorau, Robin
    et al.
    Görbe, Tamás
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Svedendahl Humble, Maria
    Improved Enantioselectivity of Subtilisin Carlsberg Towards Secondary Alcohols by Protein Engineering2018In: ChemBioChem (Print), ISSN 1439-4227, E-ISSN 1439-7633, Vol. 19, no 4, p. 338-346Article in journal (Refereed)
    Abstract [en]

    Generally, the catalytic activity of subtilisin Carlsberg (SC) for transacylation reactions with secondary alcohols in organic solvent is low. Enzyme immobilization and protein engineering was performed to improve the enantioselectivity of SC towards secondary alcohols. Possible amino-acid residues for mutagenesis were found by combining available literature data with molecular modeling. SC variants were created by site-directed mutagenesis and were evaluated for a model transacylation reaction containing 1-phenylethanol in THF. Variants showing high E values (>100) were found. However, the conversions were still low. A second mutation was made, and both the E values and conversions were increased. Relative to that shown by the wild type, the most successful variant, G165L/M221F, showed increased conversion (up to 36 %), enantioselectivity (E values up to 400), substrate scope, and stability in THF.

  • 322. Duan, Lele
    et al.
    Bozoglian, Fernando
    Mandal, Sukanta
    Stewart, Beverly
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Llobet, Antoni
    Sun, Licheng
    A molecular ruthenium catalyst with water-oxidation activity comparable to that of photosystem II2012In: Nature Chemistry, ISSN 1755-4330, E-ISSN 1755-4349, Vol. 4, no 5, p. 418-423Article in journal (Refereed)
    Abstract [en]

    Across chemical disciplines, an interest in developing artificial water splitting to O-2 and H-2, driven by sunlight, has been motivated by the need for practical and environmentally friendly power generation without the consumption of fossil fuels. The central issue in light-driven water splitting is the efficiency of the water oxidation, which in the best-known catalysts falls short of the desired level by approximately two orders of magnitude. Here, we show that it is possible to close that 'two orders of magnitude' gap with a rationally designed molecular catalyst [Ru(bda)(isoq)(2)] (H(2)bda = 2,2'-bipyridine-6,6'-dicarboxylic acid; isoq = isoquinoline). This speeds up the water oxidation to an unprecedentedly high reaction rate with a turnover frequency of >300 s(-1). This value is, for the first time, moderately comparable with the reaction rate of 100-400 s(-1) of the oxygen-evolving complex of photosystem II in vivo.

  • 323.
    Duan, Lele
    et al.
    Department of Chemistry, Royal Institute of Technology .
    Nyhlén, Jonas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Fischer, Andreas
    Department of Chemistry, Royal Institute of Technology .
    Xu, Yunhua
    Department of Chemistry, Royal Institute of Technology .
    Privalov, Timofei
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Licheng
    Department of Chemistry, Royal Institute of Technology .
    Highly Active Mononuclear Ru Catalysts for Water Oxidation: O-O Bond Formation via Direct Radical CouplingIn: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126Article in journal (Refereed)
  • 324. Dutheuil, Guillaume
    et al.
    Selander, Nicklas
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aggarwal, Varinder K.
    Direct synthesis of functionalized allylic boronic esters from allylic alcohols and inexpensive reagents and catalysts2008In: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, no 14, p. 2293-2297Article in journal (Refereed)
    Abstract [en]

    A remarkably simple and effective system for the direct conversion of allylic alcohols into high value allylic boronic esters using commercially available reagents and catalysts is described.

  • 325.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Amino acid-catalyzed synthesis of amino acid derivatives: Application and semi-synthesis of Paclitaxel, Docetaxel and their derivatives2010Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    This thesis deals with different applications of organocatalysis, where amino acid derivatives and small peptides are applied as catalysts. First, the development of environmentally friendly aldol reactions, carried out in aqueous media is illustrated. The corresponding β-hydroxy ketones are formed with ee´s up to 99%. Chapter 3 describes the ability of β3-amino acids to selectively catalyze Mannich-type reactions and govern the formation of products with high anti-selectivity (up to >19:1) and ee´s up to 99%. In the following chapter, an amino acid-catalyzed one-pot three component Mannich reaction between dihydroxyacetone and PMP-protected imines, is presented. The corresponding a,a’-dihydroxy-b-aminoketones are obtained in high yields and with 82-95% ee. Next, an aza-Morita-Baylis-Hillman reaction was investigated where L-proline is the catalyst. The reaction proceeds with excellent chemo- and enantioselectivity to give the corresponding compounds in good yields and with 97-99% ee. Finally, the last part describes development of a proline-catalyzed Mannich reation between N-acyl imines and protected α-hydroxyaldehyes, providing access to different α-hydroxy-β-amino acids in good yields and high enantioselctivity (92-99% ee). The obtained amino acids were further applied in the semisynthesis of paclitaxel and docetaxel derivatives.

  • 326.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Asymmetric Organocatalytic Aldol and Mannich Reactions Catalyzed by Amino Acid-Derivatives and Small Peptides with a Primary Amine Functionality2008Licentiate thesis, comprehensive summary (Other academic)
  • 327.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Inorganic ammonium salts as catalysts for direct aldol reactions in the presence of water2009In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 50, no 52, p. 7242-7245Article in journal (Refereed)
  • 328.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Acyclic beta-amino acid catalyzed asymmetric anti-selective Mannich-type reactions2007In: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 18, no 9, p. 1033-1037Article in journal (Refereed)
    Abstract [en]

     The ability of a primary amine containing acyclic beta(3)-amino acids to catalyze direct asymmetric anti-selective Mannich-type reactions is presented. The reactions are generally highly diastereo- and enantioselective to give the corresponding Mannich products with up to >19:1 dr (anti/syn) and 88-99% ee.

  • 329.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives2008In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 49, no 5, p. 803-807Article in journal (Refereed)
    Abstract [en]

    Highly enantioselective, amino acid-catalyzed, one-pot three-component asymmetric Mannich reactions between dihydroxyacetone, p-anisidine, and aldehydes are presented. The reactions proceeded with high chemo- and stereoselectivity and furnished the corresponding α,α′-dihydroxy-β-aminoketones in high yields with 82–95% ee.

  • 330.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schyman, Patric
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kullberg, Martin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly enantioselective organocatalytic addition of aldehydes to acylimines: Asymmetric syntheses of the paclitaxel and docetaxel side-chains and their analogs2010In: Abstracts of Papers, 239th ACS National Meeting, San Francisco, CA, United States, March 21-25, 2010, Washington, D C: American Chemical Society , 2010Conference paper (Other academic)
  • 331.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Schyman, Patric
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Physical Chemistry.
    Kullberg, Martin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 16, p. 4044-4048Article in journal (Refereed)
  • 332.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic asymmetric synthesis of the docetaxel (Taxotere) side chain: organocatalytic highly enantioselective synthesis of esterification-ready alpha-hydroxy-beta-amino acids2008In: Tetrahedron Letters, ISSN 0040-4039, Vol. 49, no 47, p. 6631-6634Article in journal (Refereed)
    Abstract [en]

    A highly enantioselective catalytic route to protected β-amino-α-hydroxy acids, such as the side chain of Taxotere, is presented. The organocatalytic asymmetric reactions between unmodified protected α-oxyaldehydes and N-Boc-protected aryl imines give the corresponding compound with up to >19:1 dr and 99–99% ee.

  • 333.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Weibiao, Zou
    Hafrén, Jonas
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    The small peptide-catalyzed direct asymmetric aldol reaction in water2006In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 4, p. 38-40Article in journal (Refereed)
  • 334.
    Dziedzic, Pawel
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Practical amino acid-catalyzed asymmetric synthesis pf protected α-hydroxy-amino aldehydes and acidsManuscript (preprint) (Other academic)
  • 335.
    Edin, Michaela
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ruthenium-catalyzed redox reactions and lipase-catalyzed asymmetric transformations of alcohols2005Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    The major part of this thesis describes the synthesis of enantiopure alcohols and diols by combining ruthenium-catalyzed redox reactions that lead to racemization or epimerization and lipase-catalyzed asymmetric trans-formations in one-pot.

    A mechanistic study of the unexpected facile formation of meso-diacetate products found in enzyme-catalyzed acetylations of alkanediols with Candida antarctica lipase B (CALB) was first performed. By deuterium labeling it was found that the formation of meso-diacetates proceeds via different mechanisms for 2,4-pentanediol and 2,5-hexanediol. Whereas the first reacts via an intramolecular acyl migration, the latter proceeds via a direct, anomalous S-acylation of the alcohol. The acyl migration occurring in the 2,4-pentanediol monoacetate was taken advantage of in asymmetric transformations of substituted 1,3-diols by combining it with a ruthenium-catalyzed epimerization and an enzymatic transesterification using CALB. The in situ coupling of these three processes results in de-epimerization and deracemization of acyclic, unsymmetrical 1,3-diols and constitutes a novel dynamic kinetic asymmetric transformation (DYKAT) concept.

    Racemization of secondary alcohols effected by a new ruthenium complex was combined in one-pot with an enzyme-catalyzed transesterification, leading to a chemoenzymatic dynamic kinetic resolution (DKR) operating at room temperature. Aromatic, aliphatic, heterocyclic and functionalized alcohols were subjected to the procedure. A mechanism for racemization by this ruthenium complex has been proposed and experimental indications for hydrogen transfer within the coordination sphere of ruthenium were found. The same ruthenium catalyst was used for epimerization in DYKAT of 1,2-diols, and a very similar complex was employed in isomerization of allylic alcohols to saturated ketones. The former method is a substrate extension of the above principle applied for DYKAT of 1,3-diols. The combination of a lipase and an organocatalyst was demonstrated by linking a lipase-catalyzed transesterification to a proline-mediated aldol reaction for the production of enantiopure (S)-β-hydroxy ketones and acetylated (R)-aldols.

  • 336.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    On the mechanism of the unexpected facile formation of meso-diacetate products in enzymatic acetylation of alkanediols2003In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, p. 2216-2222Article in journal (Refereed)
  • 337.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Córdova, Armando
    Tandem enantioselective organo- and biocatalysis: a direct entry for the synthesis of enantiomerically pure aldols2004In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 45, p. 7697-7701Article in journal (Refereed)
  • 338.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Bäckvall, Jan-E.
    Dynamic kinetic asymmetric transformation of 1,2-diols: an enantioselective synthesis of syn-1,2-diacetatesManuscript (Other academic)
  • 339.
    Edin, Michaela
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Steinreiber, Johannes
    Bäckvall, Jan-E.
    One-pot synthesis of enantiopure syn-1,3-diacetates from racemic diastereomeric mixtures of 1,3-diols by dynamic kinetic asymmetric transformation2004In: Proceedings of the National Academy of Sciences of the United States of America, ISSN 0027-8424, E-ISSN 1091-6490, Vol. 101, p. 5761-5766Article in journal (Refereed)
  • 340.
    Eklund, Robert
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Computational Analysis of Carbohydrates: Dynamical Properties and Interactions2005Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In this thesis a computational complement to experimental observables will be presented. Computational tools such as molecular dynamics and quantum chemical tools will be used to aid in the interpretation of experimentally (NMR) obtained structural data. The techniques are applied to study the dynamical features of biologically important carbohydrates and their interaction with proteins. When evaluating conformations, molecular mechanical methods are commonly used. Paper I, highlights some important considerations and focuses on the force field parameters pertaining to carbohydrate moieties. Testing of the new parameters on a trisaccharide showed promising results. In Paper II, a conformational analysis of a part of the repeating unit of a Shigella flexneri bacterium lipopolysaccharide using the modified force field revealed two major conformational states. The results showed good agreement with experimental data. In Paper III, a trisaccharide using Langevin dynamics was investigated. The approach used in the population analysis included a least-square fit technique to match T1 elaxation parameters. The results showed good agreement with experimental T-ROE build-up curves, and three states were concluded to be involved. In Paper IV, carbohydrate moieties were used in the development of prodrug candidates, to “hide” peptide opioid receptor agonists. Langevin dynamics and quantum chemical methods were employed to elucidate the structural preference of the compound. The results showed a chemical shift difference between hydrogens across the ring for the two isomers as well as a difference in the coupling constant, when taking the dynamics into account. In Paper V, the interaction of the Salmonella enteritidis bacteriophage P22 with its host bacterium, involves an initial hydrolysis of the O-antigenic polysaccharide (O-PS). Docking calculations were used to examine the binding between the Phage P22 tail-spike protein and the O-PS repeating unit. Results indicated a possible active site in conjunction with NMR measurements.

  • 341.
    Eklund, Robert
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lycknert, Kristina
    Söderman, Peter
    Widmalm, Göran
    Söderman,
    A conformational dynamics study of a-L-Rhap-(1-->2)[a-L-Rhap-(1-->3)]-a-L-Rhap-OMe in solution by NMR experiments and molecular simulationsManuscript (Other academic)
  • 342.
    Eklund, Robert
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Roscic, Maja
    Nordmark, Eva-Lisa
    Widmalm, Göran
    Horvat, Stefica
    Stereochemical assignment of diastereomeric imidazolidinone ring containing bicyclic sugar-peptide addects: NMR Spectroscopy and molecular calculations2004In: European Journal of Organic Chemistry, ISSN 1434-193X, no 22, p. 4641-4647Article in journal (Refereed)
  • 343.
    Eklund, Robert
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Widmalm, Göran
    Molecular dynamics simulations of an oligosaccharide using a force field modified for carbohydrates2003In: Carbohydrate Research, ISSN 0008-6215, Vol. 338, no 5, p. 393-398Article in journal (Refereed)
  • 344.
    Ekström, Jesper
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Transition Metal Hydrides: Biomimetic Studies and Catalytic Applications2007Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In this thesis, studies of the nature of different transition metal-hydride complexes are described. The first part deals with the enantioswitchable behaviour of rhodium complexes derived from amino acids, applied in asymmetric transfer hydrogenation of ketones. We found that the use of amino acid thio amide ligands resulted in the formation of the R-configured product, whereas the use of the corresponding hydroxamic acid- or hydrazide ligands selectively gave the S-alcohol.

    Structure/activity investigations revealed that the stereochemical outcome of the catalytic reaction depends on the ligand mode of coordination.

    In the second part, an Fe hydrogenase active site model complex with a labile amine ligand has been synthesized and studied. The aim of this study was to find a complex that efficiently catalyzes the reduction of protons to molecular hydrogen under mild conditions. We found that the amine ligand functions as a mimic of the loosely bound ligand which is part of the active site in the hydrogenase.

    Further, an Fe hydrogenase active site model complex has been coupled to a photosensitizer with the aim of achieving light induced hydrogen production. The redox properties of the produced complex are such that no electron transfer from the photosensitizer part to the Fe moiety occurs.

    In the last part of this thesis, the development of a protocol for the transfer hydrogenation of ketones to secondary alcohols without the involvement of transition metal catalysts is described. A variety of ketones were efficiently reduced in 2-propanol using catalytic amounts of alkali alkoxide under microwave irradiation.

  • 345.
    Ekström, Jesper
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Abrahamsson, Maria
    Olson, Carol
    Bergquist, Jonas
    Kanyak, Feliz B.
    Eriksson, Lars
    Sun, Licheng
    Åkermark, Björn
    Becker, Hans-Christian
    Hammarström, Leif
    Ott, Sascha
    Bio Inspired Side-on Attachment of a Ruthenium Photo-sensitizer to an Iron Hydrogenase Active Site Model2006In: Dalton Transactions, ISSN 1477-9226, no 38, p. 4599-4606Article in journal (Refereed)
  • 346.
    Ekström, Jesper
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wettergren, Jenny
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Simple and Efficient Catalytic Method for the Reduction of Ketones2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 10, p. 1609-1613Article in journal (Refereed)
    Abstract [en]

    A range of ketones was efficiently reduced in the presence of catalytic amounts of lithium isopropoxide in 2-propanol under microwave heating, with alcohol products being formed in yields up to 99 %.

  • 347.
    Endo, Yoshinori
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aerobic Lactonization of Diols by Biomimetic Oxidation2011In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 17, no 45, p. 12596-12601Article in journal (Refereed)
  • 348.
    Endo, Yoshinori
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Biomimetic Oxidative Coupling of Benzylamines and 2-Aminophenols: Synthesis of Benzoxazoles2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 43, p. 13609-13613Article in journal (Refereed)
  • 349.
    Engelmark Cassimjee, Karim
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kadow, Maria
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Wikmark, Ylva
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Svedendahl Humble, Maria
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rothstein, M. L.
    Rothstein, D. M.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A general protein purification and immobilization method on controlled porosity glass: biocatalytic applications2014In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, no 65, p. 9134-9137Article in journal (Refereed)
    Abstract [en]

    A general combined purification and immobilization method to facilitate biocatalytic process development is presented. The support material, EziG (TM), is based on controlled porosity glass (CPG) or polymer-coated versions thereof (HybCPG) and binds protein affinity tags. Biocatalytic reactions in aqueous and organic media with seven enzymes of biocatalytic interest are shown.

  • 350.
    Engelmark Cassimjee, Karim
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Manta, Bianca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A quantum chemical study of the ω-transaminase reaction mechanism2015In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 13, no 31, p. 8453-8464Article in journal (Refereed)
    Abstract [en]

    ω-Transaminases are valuable tools in biocatalysis due to their stereospecificity and their broad substrate range. In the present study, the reaction mechanism of Chromobacterium violaceum ω-transaminase is investigated by means of density functional theory calculations. A large active site model is designed based on the recent X-ray crystal structure. The detailed energy profile for the half-transamination of (S)-1-phenylethylamine to acetophenone is calculated and the involved transition states and intermediates are characterized. The model suggests that the amino substrate forms an external aldimine with the coenzyme pyridoxal-5′-phosphate (PLP), through geminal diamine intermediates. The external aldimine is then deprotonated in the rate-determining step, forming a planar quinonoid intermediate. A ketimine is then formed, after which a hemiaminal is produced by the addition of water. Subsequently, the ketone product is obtained together with pyridoxamine-5′-phosphate (PMP). In the studied half-transamination reaction the ketone product is kinetically favored. The mechanism presented here will be valuable to enhance rational and semi-rational design of engineered enzyme variants in the development of ω-transaminase chemistry.

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