Design of Organocatalysts for Asymmetric Direct Syn-Aldol Reactions

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Abstract

Two new organocatalysts 3a and 3b, derived from l-leucine and (S)-β-amino alcohols that were prepared from l-valine, were designed and afforded the direct syn-aldol reactions of a wide scope of aldehydes with various ketones with an excellent diastereomeric ratio of up to >20/1 and enantioselectivities of up to 99% ee.

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This article has been cited by 13 ACS Journal articles (5 most recent appear below).

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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 ...

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

  Reversal of Diastereoselectivity in Reactions of the Trifluoroacetaldehyde Ethyl Hemiacetal with Enamines and Imines: Metal-Free, Complementary anti- and syn-Selective Synthesis of 4,4,4-Trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

  Kazumasa Funabiki, Kei Matsunaga, Hiroshi Gonda, Hitoshi Yamamoto, Takao Arima, Yasuhiro Kubota, and Masaki Matsui
  The Journal of Organic Chemistry2011 76 (1), 285-288

  • Reversal of Diastereoselectivity in Reactions of the Trifluoroacetaldehyde Ethyl Hemiacetal with Enamines and Imines: Metal-Free, Complementary anti- and syn-Selective Synthesis of 4,4,4-Trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones

    Kazumasa Funabiki, Kei Matsunaga, Hiroshi Gonda, Hitoshi Yamamoto, Takao Arima, Yasuhiro Kubota, and Masaki Matsui
    The Journal of Organic Chemistry2011 76 (1), 285-288

    A complete reversal of diastereoselectivity was observed for reactions of the trifluoroacetaldehyde ethyl hemiacetal with enamines and imines, derived from propiophenones, that produce 4,4,4-trifluoro-1-aryl-3-hydroxy-2-methyl-1-butanones. This process ...

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

  Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

  Pengfei Li, Junling Zhao, Fengbo Li, Albert S. C. Chan, and Fuk Yee Kwong
  Organic Letters2010 12 (24), 5616-5619

  • Highly Enantioselective and Efficient Organocatalytic Aldol Reaction of Acetone and β,γ-Unsaturated α-Keto Ester

    Pengfei Li, Junling Zhao, Fengbo Li, Albert S. C. Chan, and Fuk Yee Kwong
    Organic Letters2010 12 (24), 5616-5619

    An effective organocatalytic asymmetric aldol reaction of acetone to β,γ-unsaturated α-keto ester has been developed. In the presence of 5 mol % of 9-amino (9-deoxy)-epicinchona alkaloid and 10 mol % of 4-nitrobenzoic acid, the aldol adducts containing ...

    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
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  Chiral Primary−Tertiary Diamine−Brønsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes

  Jiuyuan Li, Niankai Fu, Xin Li, Sanzhong Luo and Jin-Pei Cheng
  The Journal of Organic Chemistry2010 75 (13), 4501-4507

  • Chiral Primary−Tertiary Diamine−Brønsted Acid Salt Catalyzed Syn-Selective Cross-Aldol Reaction of Aldehydes

    Jiuyuan Li, Niankai Fu, Xin Li, Sanzhong Luo and Jin-Pei Cheng
    The Journal of Organic Chemistry2010 75 (13), 4501-4507

    Highly syn-selective cross-aldol reaction of aldehydes has remained a challenging subject in the field of aminocatalysis. To achieve this end, chiral primary amines have been explored and the primary−tertiary diamine−Brønsted acid salts are found to ...

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

  Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis

  Shenshen Hu, Jiuyuan Li, Junfeng Xiang, Jie Pan, Sanzhong Luo and Jin-Pei Cheng
  Journal of the American Chemical Society2010 132 (20), 7216-7228

  • Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis

    Shenshen Hu, Jiuyuan Li, Junfeng Xiang, Jie Pan, Sanzhong Luo and Jin-Pei Cheng
    Journal of the American Chemical Society2010 132 (20), 7216-7228

    A new approach of asymmetric supramolecular catalysis has been developed by combining the supramolecular recognition of β-cyclodextrin (β-CD) and the superior property of a chiral primary amine catalyst. The resulted β-CD enamine catalysts could ...

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

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