Stereoselective Synthesis

  • Organocatalytic Asymmetric Synthesis of trans-γ-Lactams
    S. Dong, M. Frings, D. Zhang, C. G. Daniliuc, H. Cheng, C. Bolm, Chem. Eur. J. 2017, 23, 13888–13892.

  • Design, Synthesis and Evaluation of N-(tert-butyl)-Alanine-Derived Chiral Ligands; Aspects of Reactivity and Diastereoselectivity in the Reactions with α-Amino Acids
    M. Bremerich, C. Bolm, G. Raabe, V. Soloshonok, Eur. J. Org. Chem. 2017, 3211–3221.

  • Mechanochemical enzymatic kinetic resolution of secondary alcohols under ball-milling conditions
    J. G. Hernández, M. Frings, C. Bolm, ChemCatChem 2016, 8, 1769–1772.

  • Organocatalytic Kinetic Resolution of Sulfoximines
    S. Dong, M. Frings, H. Cheng, J. Wen, D. Zhang, G. Raabe, C. Bolm, J. Am. Chem. Soc. 2016, 138, 2166 – 2169. Selected by B. List and L. Liu for Synfacts 2016, 12, 634.

  • Cinchona Alkaloid-Catalyzed Asymmetric Desymmetrization of meso Cyclic Anhydrides: The Origins of Stereoselectivity
    B. Dedeoglu, S. Catak, A. Yildirim, C. Bolm, V. Aviyente, ChemCatChem 2015, 7, 4173–4179.

  • Asymmetric Copper-Catalyzed Vinylogous Mukaiyama Michael Addition of Cyclic Dienol Silanes to Unsaturated α-Keto Phosphonates
    A.-D. Steinkamp, M. Frings, I. Thomé, I. Schiffers, C. Bolm, Chem. Eur. J. 2015, 21, 7705–7708.

  • Asymmetric Carbon Carbon Bond Formations under Solventless Conditions in Ball Mills
    M. Jörres, J. L. Aceña, V. A. Soloshonok, C. Bolm, ChemCatChem. 2015, 7, 1265–1269 (Selected as very important paper).

  • Formation of Three New Bonds and Two Stereocenters in Acyclic Systems by Zinc-Mediated Asymmetric Alkynylation of Acylsilanes, Brook Rearrangement and Ene-Allene Carbo­cyclization Reactions
    P. Smirnov, E. Katan, J. Mathew, A. Nijs, M. Karni, C. Bolm, Y. Apeloig, I. Marek, J. Org. Chem. 2014, 79, 12122–12135.

  • A New Chiral Glycine Equivalent for the Asymmetric Synthesis of α-Amino Acids under Operationally Convenient Conditions
    M. Jörres, X. Chen, J. L. Aceña, C. Merkens, C. Bolm, H. Liu, V. A. Soloshonok, Adv. Synth. Catal. 2014, 356, 2203–2208.

  • Catalytic, Asymmetric Synthesis of Phosphonic γ-(Hydroxyalkyl)butenolides with Contiguous Quaternary and Tertiary Stereogenic Centers
    M. Frings, I. Thomé, I. Schiffers, F.-F. Pan, C. Bolm, Chem. Eur. J. 2014, 20, 1691–1700.

  • One-Pot Zinc-Promoted Asymmetric Alkynylation/Brook-Type Rearrangement/Ene-Allene Cyclization: Highly Selective Formation of Three New Bonds and Two Stereocenters in Acyclic Systems
    P. Smirnov, J. Mathew, A. Nijs, E. Katan, M. Karni, C. Bolm, Y. Apeloig, I. Marek, Angew. Chem. 2013, 125, 13962–13966; Angew. Chem. Int. Ed. 2013, 52, 13717–13721. Selected by H. Yamamoto and A. Izumiseki for Synfacts 2014, 10, 269.

  • Enantioselective Nitrene Transfer to Sulfides Catalyzed by a Chiral Iron Complex
    J. Wang, M. Frings, C. Bolm, Angew. Chem. 2013, 125, 8823–8827; Angew. Chem. Int. Ed. 2013, 52, 8661–8665. Selected by H. Hayashi and Y. Shimoda for Synfacts 2013, 9, 118.

  • Organocatalytic solvent-free hydrogen bonding-mediated asymmetric Michael additions under ball milling conditions
    M. Jörres, S. Mersmann, G. Raabe, C. Bolm, Green Chem. 2013, 15, 612–616.

  • Synthesis of Planar Chiral Carbazole Derivatives bearing a [2.2]Paracyclophane Skeleton
    P. Lennartz, G. Raabe, C. Bolm, Isr. J. Chem. 2012, 52, 171–179.

  • Planar-Chiral Bis-silanols and Diols as H-Bonding Asymmetric Organocatalysts
    C. Beemelmanns, R. Husmann, D. K. Whelligan, S. Özçubukçu, C. Bolm, Eur. J. Org. Chem. 2012, 3373–3376.

  • Synthesis of Chiral Sulfoximine-based Thioureas and their Application in Asymmetric Organocatalysis
    M. Frings, I. Thomé, C. Bolm, Beilstein J. Org. Chem. 2012, 8, 1443–1451.

  • Asymmetric Michael Additions of α-Nitrocyclohexanone to Nitroalkenes Catalyzed by Natural Amino Acid-Derived Bifunctional Thioureas
    M. Jörres, I. Schiffers, I. Atodiresei, C. Bolm, Org. Lett. 2012, 14, 4518 -4521.

  • Enantioselective Organocatalytic Synthesis of Quaternary α-Amino Acids Bearing a CF3 Moiety
    R. Husmann, E. Sugiono, S. Mersmann, G. Raabe, M. Rueping, C. Bolm, Org. Lett. 2011, 13, 1044–1047.

  • Asymmetric Synthesis of S,S-Dialkyl-Substituted Sulfoximines and Related Heterocycles
    A. G. Pandey, M. J. McGrath, O. García Mancheño, C. Bolm, Synthesis 2011, 3827–3828.

  • Ephedrine- and Pseudoephedrine-Derived Thioureas in Asymmetric Michael Additions of Ketoesters and Diketones to Nitroalkenes
    A. M. Flock, A. Krebs, C. Bolm, Synlett 2010, 1219–1222.

  • Enantioenrichment by Iterative Retro-Aldol/Aldol Reaction Catalyzed by an Achiral or Racemic Base
    A. M. Flock, C. M. M. Reucher, C. Bolm, Chem. Eur. J. 2010, 16, 3918–3291.

  • C1-Symmetric Aminosulfoximines in Copper-Catalyzed Asymmetric Vinylogous Mukaiyama Aldol Reactions
    M. Frings, I. Atodiresei, Y. Wang, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 4577–4587.

  • Synthesis of Amino-Functionalized Sulfonimidamides and Their Application in the Enantioselective Henry Reaction
    M. Steurer, C. Bolm, J. Org. Chem. 2010, 75, 3301–3310.
    Selected by M. Lautens, C. Tsui for Synfacts 2010, 8, 912.

  • Enantioselective Synthesis of Highly Functionalized Amides by Copper-Catalyzed Vinylogous Mukaiyama Aldol Reaction
    M. Frings, D. Goedert, C. Bolm, Chem. Commun. 2010, 46, 5497–5499.

  • Highly enantioselective desymmetrizations of meso-anhydrides
    E. Schmitt, I. Schiffers, C. Bolm, Tetrahedron 2010, 66, 6349–6357.

  • Silylated Pyrrolidines as Catalysts for Asymmetric Michael Additions of Aldehydes to Nitroolefins
    R. Husmann, M. Jörres, G. Raabe, C. Bolm, Chem. Eur. J. 2010, 16, 12549–12552.

  • Nonlinear effects in proline-catalysed aldol reactions under solvent-free conditions based on the ternary phase behaviour of scalemic proline
    A. Bruckmann, B. Rodríguez, C. Bolm, CrystEngComm 2009, 11, 404–407.

  • Catalyzed Vinylogous Mukaiyama Aldol Reactions With Controlled Enantio- and Diastereoselectivities
    M. Frings, I. Atodiresei, J. Runsink, G. Raabe, C. Bolm, Chem. Eur. J. 2009, 15, 1566–1569.
    Selected by H. Yamamoto, J. N. Payette for Synfacts 2009, 5, 509.

  • Organocatalytic conversion of arylglyoxals into optical active mandelic acid derivatives
    E. Schmitt, I. Schiffers, C. Bolm, Tetrahedron Lett. 2009, 50, 3185–3188.

  • Enantioselective Halogenations of β-Ketoesters Catalyzed by a Chiral Copper Sulfoximine Complex
    M. Frings, C. Bolm, Eur. J. Org. Chem. 2009, 121, 4085–4090.

  • Synthesis and resolution of racemic trans-2-(N-benzyl)amino-1-cyclohexanol: Enantiomer separation by sequential use of (R)- and (S)-mandelic acid
    I. Schiffers, C. Bolm, Org. Synth. 2008, 85, 106–107.

  • Synthesis of Sulfoximine-Derived P,N-Ligands and Their Applications in Asymmetric Hydrogenation Reactions
    S.-M. Lu, C. Bolm, Adv. Synth. Catal. 2008, 350, 1101–1105.

  • C1-Symmetric Oxazolinyl-Sulfoximines as Ligands in Copper-Catalyzed Asymmetric Mukaiyama Aldol Reactions
    J. Sedelmeier, J. Hammerer, C. Bolm, Org. Lett. 2008, 10, 917–920.

  • Highly Chemo- and Enantioselective Hydrogenation of Linear α,β-Unsaturated Ketones
    S.-M. Lu, C. Bolm, Chem. Eur. J. 2008, 14, 7513–7516.

  • New chiral catalysts for C-C-bond formations, C. Bolm in New Methodologies and Techniques for a Sustainable Chemistry (Eds.: A. Mordini, F. Faigl), Springer, 2008, 85–98.

  • Highly Enantioselective Synthesis of Optically Active Ketones by Iridium-Catalyzed Asymmetric Hydrogenation
    S.-M. Lu, C. Bolm, Angew. Chem. 2008, 120, 9052–9055; Angew. Chem. Int. Ed. 2008, 47, 8920–8923.

  • Editorship of Organosulfur Chemistry in Asymmetric Synthesis (Eds.: T. Toru, C. Bolm), Wiley-VCH, Weinheim, Germany 2008 (432 pages).

  • Mechanistic Insights into Stereoselective Catalysis - The Effects of Counterions in a Cu(II)Bissulfoximine Catalyzed Diels-Alder Reaction
    C. Bolm, M. Martin, G. Gescheidt, C. Palivan, T. Stanoeva, H. Bertagnolli, M. Feth, A. Schweiger, G. Mitrikas, J. Harmer, Chem. Eur. J. 2007, 1842–1850.

  • Dimethylzinc-Mediated, Enantioselective Synthesis of Propargylic Amines
    L. Zani, T. Eichhorn, C. Bolm, Chem. Eur. J. 2007, 13, 2587–2600.

  • Diaryl methanols by Catalyzed Asymmetric Aryl Transfer Reactions onto Aldehydes Using Boronic Acids as Aryl Source
    F. Schmidt, J. Rudolph, C. Bolm, Adv. Synth. Catal. 2007, 349, 703–708.

  • Catalyzed asymmetric aryl transfer reactions (Personal Account)
    C. Bolm, in Asymmetric Synthesis with Chemical and Biological Methods (Eds.: D. Enders, K.-E. Jaeger), Wiley/VCH, Weinheim 2007, 176–196.

  • Sulfoximines as ligands in asymmetric metal catalysis (Personal Account)
    C. Bolm, in Asymmetric Synthesis with Chemical and Biological Methods (Eds.: D. Enders, K.-E. Jaeger), Wiley/VCH, Weinheim 2007, 149–176.

  • Regio- and Stereoselective Copper-Catalyzed Carbozincation Reactions of Alkynyl Sulfoximines and Sulfones
    G. Sklute, C. Bolm, I. Marek, Org. Lett. 2007, 9, 1259–1261.

  • Solvent-free asymmetric anhydride opening in a ball mill
    T. Rantanen, I. Schiffers, C. Bolm, Org. Process Res. Dev. 2007, 11, 592–597.

  • An Unprecedented Rhodium-Catalyzed Asymmetric Intermolecular Hydroacylation Reaction with Salicylaldehydes
    R. T. Stemmler, C. Bolm, Adv. Synth. Catal. 2007, 349, 1185–1198.

  • Stereoselective Anhydride Openings
    I. Atodiresei, I. Schiffers, C. Bolm, Chem. Rev. 2007, 107, 5683–5712.

  • A Highly Efficient Asymmetric Organocatalytic Aldol Reaction in a Ball Mill
    B. Rodríguez, A. Bruckmann, C. Bolm, Chem. Eur. J. 2007, 13, 4710–4722.

  • Synthesis of Novel Chiral Phosphine-Olefin Complexes and their Evaluation as Ligands in the Rhodium-Catalyzed Asymmetric 1,4-Addition
    R. T. Stemmler, C. Bolm, Synlett 2007, 1365–1370.

  • Asymmetric Enamide Hydrogenation Using Planar Chiral Cyrhetrenes
    R. T. Stemmler, C. Bolm, Tetrahedron Lett. 2007, 48, 6189–6191.

  • Application of β-Hydroxysulfoximines in Catalytic Asymmetric Phenyl Transfer Reaction for the Synthesis of Diarylmethanols
    J. Sedelmeier, C. Bolm, J. Org. Chem. 2007, 72, 8859–8862.

  • The use of chiral lithium amides in the desymmetrisation of N-trialkylsilyl dimethyl sulfoximines
    M. J. McGrath, C. Bolm, Beilstein J. Org. Chem. 2007, 3, 33.