Organocatalytic Asymmetric Transferhydrogenation of β-Nitroacrylates: Accessing β²-Amino Acids

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Abstract

We describe a highly efficient and enantioselective Hantzsch ester mediated conjugate reduction of β-nitroacrylates that is catalyzed by a Jacobsen thiourea catalyst as a key step in a new route to optically active β²-amino acids.

Citing Articles

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This article has been cited by 10 ACS Journal articles (5 most recent appear below).

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  Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation

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  Journal of the American Chemical Society2012 134 (4), 2442-2448

  • Dihydrophenanthridine: A New and Easily Regenerable NAD(P)H Model for Biomimetic Asymmetric Hydrogenation

    Qing-An Chen, Kai Gao, Ying Duan, Zhi-Shi Ye, Lei Shi, Yan Yang, and Yong-Gui Zhou
    Journal of the American Chemical Society2012 134 (4), 2442-2448

    A new and easily regenerable NAD(P)H model 9,10-dihydrophenanthridine (DHPD) has been designed for biomimetic asymmetric hydrogenation of imines and aromatic compounds. This reaction features the use of hydrogen gas as terminal reductant for the ...

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

  Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones

  Qing-An Chen, Mu-Wang Chen, Chang-Bin Yu, Lei Shi, Duo-Sheng Wang, Yan Yang, and Yong-Gui Zhou
  Journal of the American Chemical Society2011 133 (41), 16432-16435

  • Biomimetic Asymmetric Hydrogenation: In Situ Regenerable Hantzsch Esters for Asymmetric Hydrogenation of Benzoxazinones

    Qing-An Chen, Mu-Wang Chen, Chang-Bin Yu, Lei Shi, Duo-Sheng Wang, Yan Yang, and Yong-Gui Zhou
    Journal of the American Chemical Society2011 133 (41), 16432-16435

    A catalytic amount of Hantzsch ester that could be regenerated in situ by Ru complexes under hydrogen gas has been employed in the biomimetic asymmetric hydrogenation of benzoxazinones with up to 99% ee in the presence of chiral phosphoric acid. The use ...

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

  Effect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers

  Piotr Kwiatkowski, Krzysztof Dudziński, and Dawid Łyżwa
  Organic Letters2011 13 (14), 3624-3627

  • Effect of High Pressure on the Organocatalytic Asymmetric Michael Reaction: Highly Enantioselective Synthesis of γ-Nitroketones with Quaternary Stereogenic Centers

    Piotr Kwiatkowski, Krzysztof Dudziński, and Dawid Łyżwa
    Organic Letters2011 13 (14), 3624-3627

    The significant effect of hydrostatic pressure on the difficult organocatalytic 1,4-conjugate addition of nitroalkanes to prochiral sterically congested β,β-disubstituted enones is demonstrated. This approach allows for the synthesis of γ-nitroketones ...

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

  Enantioenriched Compounds via Enzyme-Catalyzed Redox Reactions

  Mélanie Hall and Andreas S. Bommarius
  Chemical Reviews2011 111 (7), 4088-4110

  • Enantioenriched Compounds via Enzyme-Catalyzed Redox Reactions

    Mélanie Hall and Andreas S. Bommarius
    Chemical Reviews2011 111 (7), 4088-4110
    Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
• 

  Enantioselective Synthesis of Chromans with a Quaternary Stereogenic Centre through Catalytic Asymmetric Cascade Reactions

  Qiu-Lin Hua, Chao Li, Xu-Fan Wang, Liang-Qiu Lu, Jia-Rong Chen, and Wen-Jing Xiao
  ACS Catalysis2011 1 (3), 221-226

  • Enantioselective Synthesis of Chromans with a Quaternary Stereogenic Centre through Catalytic Asymmetric Cascade Reactions

    Qiu-Lin Hua, Chao Li, Xu-Fan Wang, Liang-Qiu Lu, Jia-Rong Chen, and Wen-Jing Xiao
    ACS Catalysis2011 1 (3), 221-226

    A highly enantioselective cascade reaction of benzotriazoles with nitroolefin-containing enonates catalyzed by a base/acid bifunctional organocatalyst has been developed. This cascade sequence affords efficient access to densely functionalized chiral ...

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

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