Highly Enantioselective Organocatalytic Direct Aldol Reaction in an Aqueous Medium^†

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Abstract

We have demonstrated that small organic molecules 1 and 2 catalyzed the direct aldol reaction of both acyclic and cyclic ketones with different aldehydes in an excess of water/brine. Excellent enantioselectivities up to >99% and diastereoselectivities up to 99% with very good yields were obtained by using much lower catalyst loadings (0.5 mol %).

Citing Articles

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This article has been cited by 16 ACS Journal articles (5 most recent appear below).

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  Large-Scale Synthesis of Singh’s Catalyst in a One-Pot Procedure Starting from Proline

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  • Large-Scale Synthesis of Singh’s Catalyst in a One-Pot Procedure Starting from Proline

    Albrecht Berkessel, Wacharee Harnying, Nongnaphat Duangdee, Jörg-M. Neudörfl, and Harald Gröger
    Organic Process Research & Development2012 16 (1), 123-128

    A practical one-pot procedure for the preparation of Singh’s catalyst from either l-/d-proline or Boc-proline is described. The coupling partner, a chiral amino alcohol, can be prepared and used directly without purification from the corresponding amino ...

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  Direct Asymmetric Aldol Reactions Inspired by Two Types of Natural Aldolases: Water-Compatible Organocatalysts and Zn^II Complexes

  Joanna Paradowska, Monika Pasternak, Bartosz Gut, Beata Gryzło, and Jacek Mlynarski
  The Journal of Organic Chemistry2012 77 (1), 173-187

  • Direct Asymmetric Aldol Reactions Inspired by Two Types of Natural Aldolases: Water-Compatible Organocatalysts and Zn^II Complexes

    Joanna Paradowska, Monika Pasternak, Bartosz Gut, Beata Gryzło, and Jacek Mlynarski
    The Journal of Organic Chemistry2012 77 (1), 173-187

    In this article the utility of water-compatible amino-acid-based catalysts was explored in the development of diastereo- and enantioselective direct aldol reactions of a broad range of substrates. Chiral C2-symmetrical proline- and valine-based amides and ...

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• 

  Direct Asymmetric Aldol Reaction with Recyclable Fluorous Organocatalyst

  Tsuyoshi Miura, Kie Imai, Mariko Ina, Norihiro Tada, Nobuyuki Imai and Akichika Itoh
  Organic Letters2010 12 (7), 1620-1623

  • Direct Asymmetric Aldol Reaction with Recyclable Fluorous Organocatalyst

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    Organic Letters2010 12 (7), 1620-1623

    Direct asymmetric aldol reactions of aldehydes with ketones in the presence of a catalytic amount of fluorous sulfonamide 4 and trifluoroacetic acid result in the corresponding aldol products in high yields with up to 96% ee. The fluorous organocatalyst ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  A General Approach for Preparation of Polymer-Supported Chiral Organocatalysts via Acrylic Copolymerization

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  The Journal of Organic Chemistry2010 75 (5), 1620-1629

  • A General Approach for Preparation of Polymer-Supported Chiral Organocatalysts via Acrylic Copolymerization

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    The Journal of Organic Chemistry2010 75 (5), 1620-1629

    Polymer-supported chiral organocatalysts, as well as most other forms of immobilized catalysts, are traditionally prepared by a postmodification approach where modified catalyst precursors are anchored onto prefabricated polymer beads. Herein, we report ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Enamine Catalysis with Low Catalyst Loadings - High Efficiency via Kinetic Studies

  Markus Wiesner, Grégory Upert, Gaetano Angelici and Helma Wennemers
  Journal of the American Chemical Society2010 132 (1), 6-7

  • Enamine Catalysis with Low Catalyst Loadings - High Efficiency via Kinetic Studies

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    Journal of the American Chemical Society2010 132 (1), 6-7

    Kinetic studies on enamine catalysis provided insight into the rate determining step(s) of peptide catalyzed conjugate addition reactions between aldehydes and nitroolefins. They demonstrate that not enamine formation but both the reaction of the enamine ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links

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