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Synthesis of a new C2-symmetric chiral catalyst and its application in the catalytic asymmetric borane reduction of prochiral ketones

✍ Scribed by Yan Zhou; Wen-Hua Wang; Wei Dou; Xiao-Liang Tang; Wei-Sheng Liu

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
120 KB
Volume
20
Category
Article
ISSN
0899-0042

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✦ Synopsis

Abstract

A new C~2~‐symmetric chiral catalyst 3,5‐bis[(2__S__)‐(hydroxy‐diphenylmethyl)‐ pyrrolidin‐1‐ylmethyl]‐1,3,4‐oxadiazole was successfully synthesized by the reaction of 2,5‐dichloromethyl‐1,3,4‐oxadiazole with (S)‐α,α‐diphenyl‐2‐pyrrolidinemethanol, and applied to the catalytic asymmetric reduction of prochiral ketones with borane. When the catalyst loading was 1 mol %, enantiomeric excesses of up to 86.8% and 94.5% were observed in reduction of aromatic and α‐halo ketones, respectively. Chirality, 2008. © 2007 Wiley‐Liss, Inc.

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