High Performance of Rh(Phebox) Catalysts in Asymmetric Reductive Aldol Reaction:  High Anti-Selectivity

Hisao Nishiyama,* Takushi Shiomi, Yasunori Tsuchiya, and Isamu Matsuda
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan
J. Am. Chem. Soc., 2005, 127 (19), pp 6972–6973
DOI: 10.1021/ja050698m
Publication Date (Web): April 26, 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.

, hnishi@apchem.nagoya-u.ac.jp

Abstract

Abstract Image

Chiral rhodium(bisoxazolinylphenyl) complexes (1 mol %) efficiently catalyze the asymmetric reductive aldol reaction of aldehydes and α,β-unsaturated esters at 50 °C for ca. 0.5−1.0 h with several hydrosilanes to give the corresponding β-hydroxypropionates with extremely high anti-selectivity (up to 98%) and enantioselectivity (up to 96% ee). The stereochemical outcome is likely due to a chairlike cyclic transition state involving rhodium-(E)-enolate.

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History

  • Published In Issue May 18, 2005
  • Received February 2, 2005

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