Organic letters

Chiral Relay Effect: 4-Substituted 1, 3-Benzoxazol-2-(3 H)-ones as Achiral Templates for Enantioselective Diels-Alder Reactions

L Quaranta, O Corminboeuf, P Renaud

Index: Quaranta, Laura; Corminboeuf, Olivier; Renaud, Philippe Organic Letters, 2002 , vol. 4, # 1 p. 39 - 41

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Citation Number: 41

Abstract

A new strategy to control the enantioselectivity of Lewis acid catalyzed reactions has been investigated. The use of N-acryloyl-1, 3-benzoxazol-2-(3 H)-ones substituted at position 4 leads to the formation of diastereomeric complexes as a result of the presence of a chiral axis. The stereochemical outcome of the reaction is controlled by the chiral catalyst and by the chiral axis, leading to high enantioselectivity improvements and, in one case, to an ...