Catalytic Asymmetric Epoxidation of α,β-Unsaturated Esters Using an Yttrium-Biphenyldiol Complex

Hiroyuki Kakei, Riichiro Tsuji, Takashi Ohshima, and Masakatsu Shibasaki*
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku Tokyo 113-0033, Japan
J. Am. Chem. Soc., 2005, 127 (25), pp 8962–8963
DOI: 10.1021/ja052466t
Publication Date (Web): June 7, 2005
Copyright © 2005 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mshibasa@mol.f.u-tokyo.ac.jp

Abstract

Abstract Image

We succeeded in a catalytic asymmetric epoxidation reaction of α,β-unsaturated esters via a conjugate addition of an oxidant using 2−10 mol % of the yttirium-chiral biphenyldiol catalyst. A variety of substrates with β-aryl and β-alkyl substituents were epoxidized efficiently, yielding the corresponding α,β-epoxy esters in up to 97% yield and 99% ee.

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History

  • Published In Issue June 29, 2005
  • Received April 15, 2005

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