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  • 1. Agasti, Soumitra
    et al.
    Maity, Soham
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Maiti, Debabrata
    Palladium-Catalyzed Synthesis of 2,3-Disubstituted Benzofurans: An Approach Towards the Synthesis of Deuterium Labeled Compounds2015In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, no 10, p. 2331-2338Article in journal (Refereed)
    Abstract [en]

    Palladium-catalyzed oxidative annulations between phenols and alkenylcarboxylic acids produced a library of benzofuran compounds. Depending on the nature of the substitution of the phenol precursor, either 2,3-dialkylbenzofurans or 2-alkyl-3-methylene-2,3-dihydrobenzofurans can be synthesized with excellent regioselectivity. Reactions between conjugated 5-phenylpenta-2,4-dienoic acids and phenol gave 3-alkylidenedihydrobenzofuran alkaloid motifs while biologically active 7-arylbenzofuran derivatives were prepared by starting from 2-phenylphenols. More interestingly, selective incorporation of deuterium from D2O has been discovered, which offers an attractive one-step method to access deuterated compounds.

  • 2.
    Ahlsten, Nanna
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Martín-Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rhodium-catalysed coupling of allylic, homoallylic, and bishomoallylic alcohols with aldehydes and N-tosylimines: insights into the mechanism2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 16, p. 2657-2666Article in journal (Refereed)
    Abstract [en]

    The isomerisation of alkenols followed by reaction with aldehydes or N-tosylimines catalysed by rhodium complexes has been studied. The catalytically active rhodium complex is formed in situ from commercially available (cyclooctadiene)rhodium(l) chloride dimer [Rh(COD)Cl](2). The tandem process affords aldol and Mannich-type products in excellent yields. The key to the success of the coupling reaction is the activation of the catalysts by reaction with postassium tert-butoxide (t-BuOK), which promotes a catalytic cycle via alkoxides rather than rhodium hydrides. This mechanism minimises the formation of unwanted by-products. The mechanism has been studied by (1)H NMR spectroscopy and deuterium labelling experiments.

  • 3. Anderson, Mattias
    et al.
    Afewerki, Samson
    Berglund, Per
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Total Synthesis of Capsaicin Analogues from Lignin-Derived Compounds by Combined Heterogeneous Metal, Organocatalytic and Enzymatic Cascades in One Pot2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 9, p. 2113-2118Article in journal (Refereed)
    Abstract [en]

    The total synthesis of capsaicin analogues was performed in one pot, starting from compounds that can be derived from lignin. Heterogeneous palladium nanoparticles were used to oxidise alcohols to aldehydes, which were further converted to amines by an enzyme cascade system, including an amine transaminase. It was shown that the palladium catalyst and the enzyme cascade system could be successfully combined in the same pot for conversion of alcohols to amines without any purification of intermediates. The intermediate vanillyl-amine, prepared with the enzyme cascade system, could be further converted to capsaicin analogues without any purification using either fatty acids and a lipase, or Schotten-Baumann conditions, in the same pot. An aldol compound (a simple lignin model) could also be used as starting material for the synthesis of capsaicin analogues. Using l-alanine as organocatalyst, vanillin could be obtained by a retro-aldol reaction. This could be combined with the enzyme cascade system to convert the aldol compound to vanillylamine in a one-step one-pot reaction.

  • 4.
    Bielawski, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Mingzhao
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and General One-Pot Synthesis of Diaryliodonium Triflates: Optimization, Scope and Limitations2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 17-18, p. 2610-2618Article in journal (Refereed)
    Abstract [en]

    Symmetrical and unsymmetrical diaryliodonium triflates have been synthesized from both electron-deficient and electron-rich arenes and aryl iodides with mCPBA and triflic acid. A thorough investigation of the optimization, scope and limitations has resulted in an improved one-pot protocol that is fast, high-yielding, and operationally simple. The reaction has been extended to the direct synthesis of symmetrical iodonium salts from iodine and arenes, conveniently circumventing the need for aryl iodides.

  • 5. Breistein, Palle
    et al.
    Johansson, Jonas
    Ibrahem, Ismail
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    One-Step Catalytic Enantioselective a-Quaternary 5-Hydroxyproline Synthesis: An Asymmetric Entry to Highly Functionalized a-Quaternary Proline Derivatives2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 6, p. 1156-1162Article in journal (Refereed)
    Abstract [en]

    The highly enantioselective cascade reaction between N-protected a-cyanoglycine esters and a,beta-unsaturated aldehydes is disclosed. The reaction represents a one-step entry to polysubstituted 5-hydroxyproline derivatives having a quaternary a-stereocenter generally in high yields with up to >95:5 dr and 99:1 er. It is also a direct catalytic two-step entry to functionalized a-quaternary proline derivatives.

  • 6.
    Buitrago, Elina
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tinnis, Fredrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Efficient and Selective Hydrosilylation of Carbonyls Catalyzed by Iron Acetate and N-Hydroxyethylimidazolium Salts2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 1, p. 217-222Article in journal (Refereed)
    Abstract [en]

    Aromatic aldehydes, along with aryl alkyl, heteroaryl alkyl, and dialkyl ketones were efficiently reduced to their corresponding primary and secondary alcohols, respectively, in high yields, using the commercially available and inexpensive polymeric silane, polymethylhydrosiloxane (PMHS), as reducing agent. The reaction is catalyzed by in situ generated iron complexes containing hydroxyethyl-functionalized NHC ligands. Turnover frequencies up to 600 h−1 were obtained

  • 7. Coll, Mercedes
    et al.
    Ahlford, Katrin
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pamies, Oscar
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dieguez, Montserrat
    Modular Furanoside Pseudodipeptides and Thioamides, Readily Available Ligand Libraries for Metal-Catalyzed Transfer Hydrogenation Reactions: Scope and Limitations2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 2-3, p. 415-427Article in journal (Refereed)
    Abstract [en]

    Two new highly modular carbohydrate-based, pseudodipeptide and thioamide ligand libraries have been synthesized for the rhodium- and ruthenium-catalyzed asymmetric transfer hydrogenation (ATH) of prochiral ketones. These series of ligands can be prepared efficiently from easily accessible D-xylose and D-glucose. The ligand libraries contain two main ligand structures (pseudodipeptide and thioamide) that have been designed by making systematic modifications to one of the most successful ligand families developed for the ATH. As well as studying the effect of these two ligand structures on the catalytic performance, we also evaluated the effect of modifying several of the ligand parameters. We found that the effectiveness of the ligands at transferring the chiral information in the product can be tuned by correctly choosing the ligand components (ligand structure and ligand parameters). Excellent enantioselectivities (ees up to 99%) were therefore obtained in both enantiomers of the alcohol products using a wide range of substrates.

  • 8.
    Cordova, Armando
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tseggai, Abrehet
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Concise catalytic asymmetric total synthesis of biologically active tropane alkaloids2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 7, p. 1363-1372Article in journal (Refereed)
    Abstract [en]

    A general strategy for the total asymmetric synthesis of valuable tropane alkaloids by catalytic stereoselective transformations is disclosed. The power of this approach is exemplified by the concise catalytic enantioselective total syntheses of (+)-methylecgonine, (-)-cocaine and (+)-cocaine as well as the first catalytic asymmetric total syntheses of a cocaine C-1 derivative and (+)-ferruginine starting from 5-oxo-protected-a,beta-unsaturated enals using only two and three column chromatographic purification steps, respectively.

  • 9.
    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.

  • 10.
    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).

  • 11.
    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.

  • 12.
    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 %.

  • 13. Ibrahem, Ismail
    et al.
    Santoro, Stefano
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective conjugate silyl additions to α,β-unsaturated aldehydes catalyzed by combination of transition metal and chiral amine catalysts2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 2+3, p. 245-252Article in journal (Refereed)
    Abstract [en]

    We report that transition metal-catalyzed nucleophilic activation can be combined with chiral amine-catalyzed iminium activation as exemplified by the unprecedented enantioselective conjugate addition of a dimethylsilanyl group to α,β-unsaturated aldehydes. These reactions proceed with excellent 1,4-selectivity to afford the corresponding β-silyl aldehyde products 3 in high yields and up to 97:3 er using inexpensive bench stable copper salts and simple chiral amine catalysts. The reaction canalso generate a quaternary stereocenter with goodenantioselectivity. Density functional calculations are performed to elucidate the reaction mechanism and the origin of enantioselectivity.

  • 14.
    Johansson, Mikael
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Purse, Byron W.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Terasak, Osamu
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Aerobic Oxidations Catalyzed by Zeolite-Encapsulated Cobalt Salophen2008In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 350, no 11-12, p. 1807-1815Article in journal (Refereed)
    Abstract [en]

    Cobalt salophen was encapsulated in a series of zeolites with a wide variation of the silicon-to-aluminium atomic ratio and with different cations. The zeolite-cobalt salophen catalysts were prepared using the “ship-in-a-bottle technique” where the complex was synthesized in the super cage of the zeolite and therefore locked into the pocket. The encapsulated catalysts were then tested in the aerobic oxidation of hydroquinone to p-benzoquinone; the best encapsulated catalyst was shown to be an efficient electron-transfer mediator in a palladium-catalyzed aerobic oxidative carbocyclization.

  • 15.
    Kalek, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Jezowska, Martina
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Preparation of arylphosphonates by palladium(0)-catalyzed cross-coupling in the presence of acetate additives: Synthetic and mechanistic studies2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 18, p. 3207-3216Article in journal (Refereed)
    Abstract [en]

    An efficient protocol for the synthesis of arylphosphonate diesters via a palladium-catalyzed cross-coupling of H-phosphonate diesters with aryl electrophiles, promoted by acetate ions, was developed. A significant shortening of the cross-coupling time in the presence of the added acetate ions was achieved for bidentate and monodentate supporting ligands, and for different aryl electrophiles (iodo, bromo and triflate derivatives). The reaction conditions were optimized in terms of amount of the catalyst, supporting ligands, and source of the acetate ion used. Various arylphosphonates, including those of potential biological significance, were synthesized using this newly developed protocol. Some mechanistic aspects of the investigated reactions are also discussed.

  • 16.
    Kalek, Marcin
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Stawinski, Jacek
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Novel, stereoselective and stereospecific synthesis of allenylphosphonates and related compounds via palladium-catalyzed propargylic substitution2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 10, p. 1741-1755Article in journal (Refereed)
    Abstract [en]

    We have developed a novel method for the synthesis of allenylphosphonates and related compounds based on a palladium(0)-catalyzed reaction of propargylic derivatives with H-phosphonate,H-phosphonothioate, H-phosphonoselenoate, and H-phosphinateesters. The reaction is stereoselective and stereospecific, and provides a convenient entry to a vast array of allenylphosphonates and their analogues with diverse substitution patterns in the allenic moiety and at the phosphorus center. Some mechanistic aspects of this new reaction were also investigated.

  • 17.
    Lihammar, Richard
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Millet, Renaud
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    An Efficient Dynamic Kinetic Resolution of N-Heterocyclic 1,2-Amino Alcohols2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 13, p. 2321-2327Article in journal (Refereed)
    Abstract [en]

    A chemoenzymatic dynamic kinetic resolution (DKR) of N-heterocyclic amino alcohols is described. Various lipases were studied as biocatalysts for the kinetic resolution of N-heterocyclic 1,2-amino alcohols. The influence of the support of the enzymes on the enantioselectivity in the resolution of different substrates is highlighted. Various 3-acetoxypyrrolidines and -piperidines were obtained in high yield and high enantiomeric excess in efficient DKR reactions.

  • 18.
    Ma, Guangning
    et al.
    Mid Sweden University, Department of Natural Sciences, Engineering and Mathematics.
    Bartoszewicz, Agnieszka
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Mid Sweden University, Department of Natural Sciences, Engineering and Mathematics.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Highly enantioselective co-catalytic direct aldol reactions by combination of hydrogen-bond donating and acyclic amino acid catalysts2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 17, p. 3114-3122Article in journal (Refereed)
    Abstract [en]

    Highly enantioselective co-catalytic direct aldol reactions by a combination of simple hydrophobic acyclic amino acid and hydrogen-bond donating catalysts are presented. The corresponding aldol products are formed in high yields with high regio-, diastereo- (anti or syn) and enantioselectivity (up to 99.5:0.5 er). The catalyst loadings can be decreased to as little as 2 mol%.

  • 19. Ma, Guangning
    et al.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Kubik, Grzegorz
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Leifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Achiral Co-Catalyst Induced Switches in Catalytic Asymmetric Reactions on Racemic Mixtures (RRM): From Stereodivergent RRM to Stereoconvergent Deracemization by Combination of Hydrogen Bond Donating and Chiral Amine Catalysts2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 14-15, p. 2865-2872Article in journal (Refereed)
    Abstract [en]

    A stereochemical divergent approach for the highly enantioselective synthesis of distinct bicyclic products with multiple stereocenters from a racemate using a single chiral catalyst is disclosed. It is based on switches of the overall reaction pathways in the chiral amine-catalyzed cascade reactions between racemic ?-nitro ketones and a,beta-unsaturated aldehydes using different achiral co-catalysts. The utility of the method is exemplified by the highly diasteroselective switch and stereoconvergent deracemization process by combination of chiral amine and achiral hydrogen-bond-donating catalysts.

  • 20. Margalef, Jèssica
    et al.
    Slagbrand, Tove
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tinnis, Fredrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Umeå University, Sweden.
    Diéguez, Montserrat
    Pàmies, Oscar
    Third-Generation Amino Acid Furanoside-Based Ligands from d-Mannose for the Asymmetric Transfer Hydrogenation of Ketones: Catalysts with an Exceptionally Wide Substrate Scope2016In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 358, no 24, p. 4006-4018Article in journal (Refereed)
    Abstract [en]

    A modular ligand library of -amino acid hydroxyamides and thioamides was prepared from 10 different N-tert-butyloxycarbonyl-protected -amino acids and three different amino alcohols derived from 2,3-O-isopropylidene--d-mannofuranoside. The ligand library was evaluated in the half-sandwich ruthenium- and rhodium-catalyzed asymmetric transfer hydrogenation of a wide array of ketone substrates, including simple as well as sterically demanding aryl alkyl ketones, aryl fluoroalkyl ketones, heteroaromatic alkyl ketones, aliphatic, conjugated and propargylic ketones. Under the optimized reaction conditions, secondary alcohols were obtained in high yields and in enantioselectivities up to >99%. The choice of ligand/catalyst allowed for the generation of both enantiomers of the secondary alcohols, where the ruthenium-hydroxyamide and the rhodium-thioamide catalysts act complementarily towards each other. The catalytic systems were also evaluated in the tandem isomerization/asymmetric transfer hydrogenation of racemic allylic alcohols to yield enantiomerically enriched saturated secondary alcohols in up to 98% ee. Furthermore, the catalytic tandem -alkylation/asymmetric transfer hydrogenation of acetophenones and 3-acetylpyridine with primary alcohols as alkylating and reducing agents was studied. Secondary alcohols containing an elongated alkyl chain were obtained in up to 92% ee.

  • 21.
    Pace, Vittorio
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry. University of Vienna, Austria.
    Holzer, Wolfgang
    Olofsson, Berit
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Increasing the Reactivity of Amides towards Organometallic Reagents: An Overview2014In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 356, no 18, p. 3697-3736Article, review/survey (Refereed)
    Abstract [en]

    The nucleophilic addition of carbon nucleophiles to amides has traditionally been a difficult task, both due to reactivity and selectivity problems. When successful, these processes would represent straightforward routes towards carbonyl-type or amine compounds, depending on the fate of the generated tetrahedral intermediate. The direct addition of nucleophiles to amides for the preparation of ketones has been studied and applied to the syntheses of several natural products. On the other hand, the addition of nucleophiles to amides to obtain substituted amines represented a major challenge, and only scattered applications on particular substrates have appeared. Initial improvements were based on the activation of amides by introduction of particular substituents, such as in N-methoxy amides (Weinreb amides) or electron-withdrawing groups able to increase the carbon nucleophilicity. Although these strategies facilitate the introduction of nucleophiles, chemoselectivity issues arise when additional electrophilic moieties (i.e., carbonyls) are present, thus decreasing the versatility of the methods. In recent years, important advancements towards fully chemoselective methods have been realized. The capture of tetrahedral intermediates with acids generates highly electrophilic iminium species able to undergo chemoselective additions of various nucleophiles, thus accessing substituted amines. Alternatively, the in situ generation of an iminium triflate ion allows highly chemoselective additions of nucleophiles, yielding amines, ketones or ketimines. Also thioamides can be used as precursors of ketones or alpha-substituted amines. The success of the above methodologies is further showcased by the application in various syntheses of natural products or biologically active molecules.

  • 22. Payer, Stefan E.
    et al.
    Sheng, Xiang
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Pollak, Hannah
    Wuensch, Christiane
    Steinkellner, Georg
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Glueck, Silvia M.
    Faber, Kurt
    Exploring the Catalytic Promiscuity of Phenolic Acid Decarboxylases: Asymmetric, 1,6-Conjugate Addition of Nucleophiles Across 4-Hydroxystyrene2017In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 359, no 12, p. 2066-2075Article in journal (Refereed)
    Abstract [en]

    The catalytic promiscuity of a ferulic acid decarboxylase from Enterobacter sp. (FDC_Es) and phenolic acid decarboxylases (PADs) for the asymmetric conjugate addition of water across the C=C bond of hydroxystyrenes was extended to the N-, C-and S-nucleophiles methoxyamine, cyanide and propanethiol to furnish the corresponding addition products in up to 91% ee. The products obtained from the biotransformation employing the most suitable enzyme/nucleophile pairs were isolated and characterized after optimizing the reaction conditions. Finally, a mechanistic rationale supported by quantum mechanical calculations for the highly (S)selective addition of cyanide is proposed.

  • 23. Pàmies, Oscar
    et al.
    Diéguez, Montserrat
    Bäckvall, Jan-E.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Artificial Metalloenzymes in Asymmetric Catalysis: Key Developments and Future Directions2015In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, no 8, p. 1567-1586Article in journal (Refereed)
    Abstract [en]

    Artificial metalloenzymes combine the excellent selective recognition/binding properties of enzymes with transition metal catalysts, and therefore many asymmetric transformations can benefit from these entities. The search for new successful strategies in the construction of metal-enzyme hybrid catalysts has therefore become a very active area of research. This review discusses all the developed strategies and the latest advances in the synthesis and application in asymmetric catalysis of artificial metalloenzymes with future directions for their design, synthesis and application (Sections 2-4). Finally, advice is presented (to the non-specialist) on how to prepare and use artificial metalloenzymes (Section 5).

  • 24.
    Rios, Ramón
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sundén, Henrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Vesely, Jan
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A simple organocatalytic enantioselective cyclopropanation of alpha-beta-unsaturated aldehydes2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 1028-1032Article in journal (Refereed)
  • 25.
    Sanz-Marco, Amparo
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Možina, Štefan
    Martinez-Erro, Samuel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Iskra, Jernej
    Martín‐Matute, Belén
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of alpha-Iodoketones from Allylic Alcohols through Aerobic Oxidative Iodination2018In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 360, no 20, p. 3884-3888Article in journal (Refereed)
    Abstract [en]

    An efficient method for the synthesis of alpha-iodoketones from allylic alcohols and elemental iodine is reported. We show in this paper that the isomerization of allylic alcohols catalyzed by iridium(III) complexes can be combined with an aerobic oxidative iodination protocol, resulting in a straightforward method for the synthesis of a wide range of alpha-iodoketones as single constitutional isomers and in high yields under mild reaction conditions.

  • 26.
    Seenivasaperumal, Muthu
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Federsel, Hans-Jürgen
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Mechanism of the asymmetric sulfoxidation in the esomeprazole process: Effects of the imidazole backbone for the enantioselection2009In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 351, no 6, p. 903-919Article in journal (Refereed)
  • 27.
    Selander, Nicklas
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Szabó, Kálmán J.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Synthesis of stereodefined substituted cycloalkenes by a one-pot catalytic boronation-allylation-metathesis sequence2008In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 350, no 13, p. 2045-2051Article in journal (Refereed)
    Abstract [en]

    Stereodefined cyclohexene and cyclopentene derivatives were prepared by the coupling of allylic alcohols and other allylic precursors with unsaturated aldehydes. These reactions are based on a multicatalytic one-pot approach involving palladium pincer complex-catalyzed boronation, allylation and ring-closing metathesis reactions. This reaction sequence can be performed in an operationally simple procedure affording the cycloalkene products in high overall yields and excellent regio- and stereoselectivities. The presented procedure has a broad synthetic scope and high functional group tolerance, which allows the synthesis of bicyclic lactone and spirane skeletons and various substitution patterns including hydroxy, silyl, vinyl, allyl, and sulfonyl groups. The studied catalytic one-pot reactions involve up to three individual processes performed by up to four acid- and transition metal-catalyzed events.

  • 28.
    Slagbrand, Tove
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Kervefors, Gabriella
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tinnis, Fredrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Umeå University, Sweden.
    An Efficient One-pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides2017In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 359, no 11, p. 1990-1995Article in journal (Refereed)
    Abstract [en]

    A Mo(CO)(6) (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated.

  • 29.
    Strübing, Dirk
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Krumlinde, Patrik
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Piera, Julio
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Bäckvall, Jan-Erling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic resolution of primary alcohols with an unfunctionalized stereogenic center in the beta-position2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 1577-1581Article in journal (Refereed)
  • 30.
    Sundén, Henrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramón
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Eriksson, Lars
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A highly enantioselective catalytic domino aza-Michael/aldol reaction: one-pot organocatalytic asymmetric synthesis of 1,2-dihydroquinolidines2007In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, p. 827-832Article in journal (Refereed)
  • 31.
    Tinnis, Fredrik
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lundberg, Helena
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Adolfsson, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Direct Catalytic Formation of Primary and Tertiary Amides from Non-Activated Carboxylic Acids, Employing Carbamates as Amine Source2012In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 354, no 13, p. 2531-2536Article in journal (Refereed)
    Abstract [en]

    The operationally simple titanium(IV)- or zirconium(IV)-catalyzed direct amidation of non-activated carboxylic acids with ammonium carbamates generates primary, and tertiary N,N-dimethyl-substituted amides in good to excellent yields.

  • 32.
    Xu, Chao
    et al.
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Incerti-Pradillos, Celia
    Córdova, Oscar
    Guo, Peng
    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.
    Hedin, Niklas
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
    The Use of Porous Palladium(II)-polyimine in Cooperatively-catalyzed Highly Enantioselective Cascade Transformations2015In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 357, no 9, p. 2150-2156Article in journal (Refereed)
    Abstract [en]

    Porous organic polymers have prospects as functional substrates for catalysis, with quite different molecular properties from inorganic substrates. Here we disclose for the first time that porous palladium(II)-polyimines are excellent catalysts for cooperatively catalyzed and enantioselective cascade reactions. In synergy with a chiral amine co-catalyst, polysubstituted cyclopentenes and spirocyclic oxindoles, including the all-carbon quaternary stereocenter, were synthesized in high yields. High diastereo- and enantioselectivities were achieved for these dynamic kinetic asymmetric transformations (DYKAT) of enals with propargylic nucleophiles.

  • 33.
    Zhao, Gui-Ling
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Korotvicka, Ales
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    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.
    Asymmetric synthesis of Maraviroc (UK-427,857)2010In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 352, no 13, p. 2291-2298Article in journal (Refereed)
    Abstract [en]

    The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral β-amino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.

  • 34. Číhalová, Sylva
    et al.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Veselý, Jan
    Asymmetric Aza-Morita–Baylis–Hillman-type reactions: The highly enantioselective reaction between unmodified α,β-unsaturated aldehydes and N-acylimines by organo-co-catal2011In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 353, no 7, p. 1096-1108Article in journal (Refereed)
    Abstract [en]

    The highly enantioselective organo-co-catalytic aza-Morita–Baylis–Hillman (MBH)-type reaction between N-carbamate-protected imines and α,β-unsaturated aldehydes has been developed. The organic co-catalytic system of proline and 1,4-diazabicyclo[2.2.2]octane (DABCO) enables the asymmetric synthesis of the corresponding N-Boc- and N-Cbz-protected β-amino-α-alkylidene-aldehydes in good to high yields and up to 99% ee. In the case of aza-MBH-type addition of enals to phenylprop-2-ene-1-imines, the co-catalytic reaction exhibits excellent 1,2-selectivity. The organo-co-catalytic aza-MBH-type reaction can also be performed by the direct highly enantioselective addition of α,β-unsaturated aldehydes to bench-stableN-carbamate-protected α-amidosulfones to give the corresponding β-amino-α-alkylidene-aldehydes with up to 99% ee.The organo-co-catalytic aza-MBH-type reaction is also an expeditious entry to nearly enantiomerically pure β-amino-α-alkylidene-amino acids and β-amino-α-alkylidene-lactams (99% ee). The mechanism and stereochemistry of the chiral amine and DABCO co-catalyzed aza-MBH-type reaction arealso discussed.

1 - 34 of 34
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