Catalytic Enantio- and Diastereoselective Aldol Reactions of Glycine-Derived Silicon Enolate with Aldehydes:  An Efficient Approach to the Asymmetric Synthesis of anti-β-Hydroxy-α-Amino Acid Derivatives

Jun Kobayashi, Masayuki Nakamura, Yuichiro Mori, Yasuhiro Yamashita, and Shū Kobayashi*
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
J. Am. Chem. Soc., 2004, 126 (30), pp 9192–9193
DOI: 10.1021/ja047597t
Publication Date (Web): July 13, 2004
Copyright © 2004 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.

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

Abstract

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We have developed an efficient method for the asymmetric synthesis of anti-β-hydroxy-α-amino acid derivatives based on highly enantio- and diastereoselective aldol reactions of the silicon enolate derived from N-trifluoroacetylglycinate with aldehydes using a chiral zirconium catalyst. The resulting N-trifluoroacetyl group is easily cleaved under either acidic or basic conditions and can be used directly as a protecting group for further transformations.

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History

  • Published In Issue August 04, 2004
  • Received April 26, 2004

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