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  • 1. Afewerki, Samson
    et al.
    Breistein, Palle
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic enantioselective β -alkylation of α,β-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: Total synthesis of bisabolane sesquiterpenes2011In: Chemistry: a European Journal, ISSN 0947-6539, Vol. 17, no 32, p. 8784-8788Article in journal (Refereed)
  • 2. 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.

  • 3.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles2013Doctoral thesis, comprehensive summary (Other academic)
    Abstract [en]

    In biological systems, most of the active organic molecules are chiral. Some of the main constituents of living organisms are amino acids and sugars. They exist predominantly in only one enantiomerically pure form. For example, our proteins are built-up by L-amino acids and as a consequence they are enatiomerically pure and will interact in different ways with enantiomers of chiral molecules. Indeed, different enantiomers or diastereomers of a molecule could often have a drastically different biological activity. It is of paramount importance in organic synthesis to develop new routes to control and direct the stereochemical outcome of reactions. The aim of this thesis is to investigate new protocols for the synthesis of complex chiral molecules using simple, environmentally friendly proline-based organocatalysts. We have investigated, the aziridination of linear and branched enals, the stereoselective synthesis of β-amino acids with a carbene co-catalyst, the synthesis of pyrazolidines, the combination of heterogeneous transition metal catalysis and amine catalysis to deliver cyclopentenes bearing an all-carbon quaternary stereocenter and a new heterogeneous dual catalyst system for the carbocyclization of enals. The reactions presented in this thesis afforded the corresponding products with high levels of chemo-, diastero- and enantioselectivity.

    Download full text (pdf)
    PhD Thesis Luca Deiana
  • 4.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Palo-Nieto, Carlos
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Verho, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Johnston, Eric V.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University.
    Highly Enantioselective Cascade Transformations by Merging Heterogeneous Transition Metal Catalysis with Asymmetric Aminocatalysis2012In: Scientific Reports, E-ISSN 2045-2322, Vol. 2, p. 851-Article in journal (Refereed)
    Abstract [en]

    The concept of combining heterogeneous transition metal and amine catalysis for enantioselective cascade reactions has not yet been realized. This is of great advantage since it would allow for the recycling of expensive and non-environmentally friendly transition metals. We disclose that the use of a heterogeneous Pd-catalyst in combination with a simple chiral amine co-catalyst allows for highly enantioselective cascade transformations. The preparative power of this process has been demonstrated in the context of asymmetric cascade Michael/carbocyclization transformations that delivers cyclopentenes bearing an all carbon quaternary stereocenters in high yields with up to 30: 1 dr and 99% ee. Moreover, a variety of highly enantioselective cascade hetero-Michael/carbocyclizations were developed for the one-pot synthesis of valuable dihydrofurans and pyrrolidines (up to 98% ee) by using bench-stable heterogeneous Pd and chiral amines as co-catalysts.

  • 5.
    Deiana, Luca
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Rios, Ramon
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Catalytic asymmetric aziridination of α, β- unsaturated aldehydes2011In: Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, August 28-September 1, 2011, American Chemical Society , 2011Conference paper (Other academic)
    Abstract [en]

    The development, scope and application of the highly enantioselective organocatalytic aziridination of a, b- unsaturated aldehydes is presented. The aminocatalytic aziridination of a, b- unsaturated aldehydes enables the asymmetric formation of b-formylaziridines with up to >19:1 dr and 99% ee. The aminocatalytic aziridination of a-monosobstituted enals gives access to terminal a-substituted-a-formyl aziridines in high yields and up to 99% ee. In the case of the organocatalytic aziridination of disubstituted a, b-unsaturated aldehydes, the transformations gives nearly enantiomeric pure b-formyl-functionalized aziridine products. A higly enantioselective one-pot cascade sequence based on combination of asymmetric amine and N-heterocyclic carbene catalysis is also disclosed. This transformation gives the corresponding N-Boc and N-Cbz protected b-amino acid esters with ee´s ranging from 92-99%.

  • 6.
    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)
  • 7.
    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.

  • 8.
    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.

  • 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.
    Cordova, Oscar
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Afewerki, Samson
    Zhang, Renyun
    Córdova, 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.

  • 10.
    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.

  • 11.
    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%

  • 12.
    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.
    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, Sweden.
    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.

  • 13.
    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).

  • 14.
    Jiang, Yan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Alimohammadzadeh, Rana
    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).
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-Pot2018In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 9, p. 1158-1164Article in journal (Refereed)
    Abstract [en]

    A versatile and highly stereoselective synthetic route to functionalized bi- and tricyclic lactams (up to > 20:1 dr and 99% ee) in one pot from simple starting materials (allylic alcohols, enals, diamines and amino alcohols) using cascade transformations promoted by chiral amine/BrOnsted or metal/chiral amine/BrOnsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal oxidant for the latter relay catalysis approach.

  • 15.
    Jiang, Yan
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhang, Kaiheng
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Total Asymmetric Synthesis of Quinine, Quinidine, and Analogues via Catalytic Enantioselective Cascade Transformations2019In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 35, p. 6016-6023Article in journal (Refereed)
    Abstract [en]

    A catalytic asymmetric strategy for the total synthesis of quinuclidine natural products, which includes the completed enantioselective synthesis of the classical targets quinine and quinidine is disclosed. It is based on catalytic asymmetric cascade transformations, which paves the road for the synthesis of both enantiomers of the crucial C4 stereocenter with high enantioselectivity (up to 99 % ee) in one pot. Next, developing a route to all possible stereoisomers of a common early-stage intermediate sets the stage for the total synthesis of different enantiomers or epimers of quinine, quinidine and analogues with high selectivity.

  • 16.
    Lin, Shuangzheng
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Tseggai, Abrehet
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Concise Total Synthesis of Dihydrocorynanthenol, Protoemetinol, Protoemetine, 3-epi-Protoemetinol and Emetine2012In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 2, p. 398-408Article in journal (Refereed)
    Abstract [en]

    A concise asymmetric assembly of secologanine tryptamine and dopamine alkaloids by means of a one-pot three-component cascade reaction methodology is disclosed. This is demonstrated by the expeditious total syntheses of (-)-dihydrocorynanthenol, (-)-protoemetinol, (-)-protoemetine, (-)-3-epi-protoemetinol, and emetine (3-6 steps). The biomimetic synthetic strategy involved the following key steps: (i) One-pot three-component highly enantioselective catalytic Michael/Pictet-Spengler/lactamization cascade reactions; (ii) One-pot tandem Swern oxidation/Wittig sequences; (iii) One-pot tandem hydrogenation sequences.

  • 17.
    Lin, Shuangzheng
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    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.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic one-pot three-component catalytic asymmetric transformation by combination of hydrogen-bond-donating and amine catalysts2011In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 50, no 33, p. 7624-7630Article in journal (Refereed)
  • 18.
    Lin, Shuangzheng
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    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).
    Zhang, Qiong
    Leijonmarck, Hans
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dynamic kinetic asymmetric domino oxa-Michael/carbocyclization by combination of transition-metal and amine catalysis: catalytic enantioselective synthesis of dihydrofurans2010In: Chemistry - A European Journal, ISSN 0947-6538, Vol. 16, no 47, p. 13930-13934Article in journal (Refereed)
  • 19. Ma, Guangning
    et al.
    Afewerki, Samson
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Palo-Nieto, Carlos
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Liu, Leifeng
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK), Inorganic and Structural Chemistry.
    Ibrahem, Ismail
    Cordova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    A Palladium/Chiral Amine Co-catalyzed Enantioselective Dynamic Cascade Reaction: Synthesis of Polysubstituted Carbocycles with a Quaternary Carbon Stereocenter2013In: Angewandte Chemie International Edition, ISSN 1433-7851, E-ISSN 1521-3773, Vol. 52, no 23, p. 6050-6054Article in journal (Refereed)
  • 20.
    Santoro, Stefano
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    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.
    Himo, Fahmi
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry. Mid Sweden University, Sweden.
    Mechanism of Palladium/Amine Cocatalyzed Carbocyclization of Aldehydes with Alkynes and Its Merging with Pd Oxidase Catalysis2014In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 4, no 12, p. 4474-4484Article in journal (Refereed)
    Abstract [en]

    The reaction mechanism for the palladium and amine cocatalyzed carbocyclization of aldehydes with alkynes has been investigated by means of density functional theory calculations and experiments. The Pd/amine cocatalyzed transformation is a carbocyclization of in situ generated enaminynes where the C-C bond-forming step is most likely promoted by a Pd(II) species. Notably, the latent Pd(O)/Pd(Ip catalytic redox cycle of this metal/organo cooperative catalytic reaction can be merged with catalytic direct aerobic alcohol oxidation (Pd oxidase catalysis).

  • 21.
    Ullah, Farman
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhao, Gui-Ling
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhu, Mingzhao
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Dziedzic, Pawel
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ibrahem, Ismail
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hammar, Peter
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Department of Structural Chemistry. Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Enantioselective organocatalytic conjugate addition of fluorocarbon nucleophiles to α,β-unsaturated aldehydes2009In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 15, no 39, p. 10013-10017Article in journal (Refereed)
    Abstract [en]

    A highly chemo- and enantioselective organocatalytic addition of fluorocarbon nucleophiles, such as 1-fluoro-bis(phenylsulfonyl)methane, toα,β-unsaturated aldehydes is presented (see scheme). The reactions are catalyzed by simple chiral amines and give access to optically active fluorine derivatives in good yields and up to 95 % ee. Notably, the methodology can be applied to the formation of a chiral quaternary carbon center bearing a fluorine atom with high enantioselectivity.

  • 22.
    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.

  • 23.
    Zhao, Gui-Ling
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Hafrén, Jonas
    Deiana, Luca
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Córdova, Armando
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Heterogeneous "organoclick" derivatization of polysaccharides: Photochemical thiol-ene click modification of solid cellulose2010In: Macromolecular rapid communications, ISSN 1022-1336, E-ISSN 1521-3927, Vol. 31, no 8, p. 740-744Article in journal (Refereed)
    Abstract [en]

    A simple and direct method for derivatization of solid polysaccharides is presented. The novel methodology is based on the combination of organic acid-catalyzed esterification or etherification and photochemical thiol-ene click derivatization of a heterogeneous polysaccharide. The solid cellulose was “organoclick” modified with aryl, alkyl and polyester groups, respectively. The modification allows for a highly modular and metal free surface modification of solid polysaccharides.

  • 24.
    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.

  • 25.
    Zhao, Gui-Ling
    et al.
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Ullah, Farman
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Luca, Deiana
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Lin, Shuangzheng
    Stockholm University, Faculty of Science, Department of Organic Chemistry.
    Zhang, Qiong
    Sun, Junliang
    Stockholm University, Faculty of Science, Department of Physical, Inorganic and Structural Chemistry, Structural Chemistry.
    Ibrahem, Ismail
    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.
    Dynamic kinetic asymmetric transformation (DYKAT) by combined amine- and transition-metal-catalyzed enantioselective cycloisomerization2010In: Chemistry: a European Journal, ISSN 0947-6539, Vol. 16, no 5, p. 1585-1591Article in journal (Refereed)
1 - 25 of 25
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