Organocatalytic Asymmetric Transfer Hydrogenation of Nitroolefins

• Abstract
• Full Text HTML
• Hi-Res PDF[62 KB]
• PDF w/ Links[149 KB]

• Supporting Info
• Figures
• Citing Articles

Your current credentials do not allow retrieval of the full text.

Purchase the full-text

• PDF/HTML,
  figures/images,
  references and tables,
  (where available)

Abstract

We describe a highly efficient and highly enantioselective Hantzsch ester mediated conjugate transfer hydrogenation of β,β-disubstituted nitroolefins that is catalyzed by a Jacobsen-type thiourea catalyst.

Citing Articles

View all 69 citing articles

Citation data is made available by participants in CrossRef's Cited-by Linking service. For a more comprehensive list of citations to this article, users are encouraged to perform a search in SciFinder.

This article has been cited by 15 ACS Journal articles (5 most recent appear below).

• 

  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

  • 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
• 

  What Are the Differences between Ascorbic Acid and NADH as Hydride and Electron Sources in Vivo on Thermodynamics, Kinetics, and Mechanism?

  Xiao-Qing Zhu, Yuan-Yuan Mu, and Xiu-Tao Li
  The Journal of Physical Chemistry B2011 115 (49), 14794-14811

  • What Are the Differences between Ascorbic Acid and NADH as Hydride and Electron Sources in Vivo on Thermodynamics, Kinetics, and Mechanism?

    Xiao-Qing Zhu, Yuan-Yuan Mu, and Xiu-Tao Li
    The Journal of Physical Chemistry B2011 115 (49), 14794-14811

    Ascorbic acid (AscH2) and dihydronicotinamide adenine dinucleotide (NADH) are two very important natural redox cofactors, which can be used as hydride, electron, and hydrogen atom sources to take part in many important bioreduction processes in vivo. The ...

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

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  Zhiguo Zhang, Katharina M. Lippert, Heike Hausmann, Mike Kotke, and Peter R. Schreiner
  The Journal of Organic Chemistry2011 76 (23), 9764-9776

  • Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

    Zhiguo Zhang, Katharina M. Lippert, Heike Hausmann, Mike Kotke, and Peter R. Schreiner
    The Journal of Organic Chemistry2011 76 (23), 9764-9776

    We report a new thiourea–Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric ...

    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

SciFinder Links

• Get Reference Detail
• Get Substances
• Get Reactions
• Get Cited
• Get Citing