Catalytic Asymmetric Epoxidation of Cyclic Enones

Xingwang Wang, Corinna M. Reisinger, Benjamin List
Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim an der Ruhr, Germany
J. Am. Chem. Soc., 2008, 130 (19), pp 6070–6071
DOI: 10.1021/ja801181u
Publication Date (Web): April 19, 2008
Copyright © 2008 American Chemical Society

Abstract

Abstract Image

A highly enantioselective epoxidation of cyclic enones with hydrogen peroxide has been developed that is catalyzed by chiral primary amine salts.

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This article has been cited by 22 ACS Journal articles (5 most recent appear below).

  • Cover Image

    Theoretical Investigation on the Chiral Diamine-Catalyzed Epoxidation of Cyclic Enones: Mechanism and Effects of Cocatalyst

    Ping-Li Lv, Rong-Xiu Zhu, Dong-Ju Zhang, Chong-Gang Duan, and Cheng-Bu Liu
    The Journal of Physical Chemistry A2012 116 (4), 1251-1260
    • Theoretical Investigation on the Chiral Diamine-Catalyzed Epoxidation of Cyclic Enones: Mechanism and Effects of Cocatalyst

      Ping-Li Lv, Rong-Xiu Zhu, Dong-Ju Zhang, Chong-Gang Duan, and Cheng-Bu Liu
      The Journal of Physical Chemistry A2012 116 (4), 1251-1260

      The asymmetric epoxidation of 2-cyclohexen-1-one with aqueous H2O2 as oxidant, 1,2-diaminocyclohexane as catalyst, and a Brønsted acid trifluoroacetic acid (TFA) as cocatalyst has been studied by performing density functional theory calculations. It is ...

  • Cover Image

    Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters

    Aijun Lin, Junying Wang, Haibin Mao, Huiming Ge, Renxiang Tan, Chengjian Zhu, and Yixiang Cheng
    Organic Letters2011 Article ASAP
    • Organocatalytic Asymmetric Michael-Type/Wittig Reaction of Phosphorus Ylides: Synthesis of Chiral α-Methylene-δ-Ketoesters

      Aijun Lin, Junying Wang, Haibin Mao, Huiming Ge, Renxiang Tan, Chengjian Zhu, and Yixiang Cheng
      Organic Letters2011 Article ASAP

      An asymmetric Michael-type reaction of phosphorus ylides and α,β-unsaturated ketones under the catalysis of a chiral ion pair catalyst has been described. The ion pair catalyst containing a chiral counteranion was prepared by simply mixing 9-amino-(9-...

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    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 Article ASAP
    • 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 Article ASAP

      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 ...

  • Cover Image

    Iron-Catalyzed Asymmetric Epoxidation of β,β-Disubstituted Enones

    YASUHIRO NISHIKAWA and Hisashi Yamamoto
    Journal of the American Chemical Society 0 (ja),
    • Iron-Catalyzed Asymmetric Epoxidation of β,β-Disubstituted Enones

      YASUHIRO NISHIKAWA and Hisashi Yamamoto
      Journal of the American Chemical Society 0 (ja),

      The combination of Fe(OTf)2 and novel phenanthroline ligands enables the catalytic asymmetric epoxidation of acyclic β,β-disubstituted enones which have been heretofore inaccessible substrate classes. The reactions provide highly enantioenriched α,β-...

  • Cover Image

    Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

    Piotr Kwiatkowski, Teresa D. Beeson, Jay C. Conrad, and David W. C. MacMillan
    Journal of the American Chemical Society2011 133 (6), 1738-1741
    • Enantioselective Organocatalytic α-Fluorination of Cyclic Ketones

      Piotr Kwiatkowski, Teresa D. Beeson, Jay C. Conrad, and David W. C. MacMillan
      Journal of the American Chemical Society2011 133 (6), 1738-1741

      The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new ...

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History

  • Published In Issue May 14, 2008
  • Article ASAPApril 19, 2008
  • Received: February 17, 2008

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