Kinetic resolution via semipinacol rearrangement of alpha-hydroxy epoxides: a new method for asymmetric synthesis of alpha-hydroxy epoxides and beta-hydroxy ketones containing an alpha-quaternary carbon

摘要

A new method for the enantioselective preparation of beta-hydroxy ketones containing a stereogenic quaternary carbon center and tertiary alpha-hydroxy epoxides has been developed on the basis of kinetic resolution of racemic tertiary alpha-hydroxy epoxide via semipinacol rearrangement using the chiral catalyst Ti[(R)/(S)-BINOL](2). The effect of the structure of the migrating group on the enantioselectivity of the reaction is also discussed. (C) 2002 Elsevier Science Ltd. All rights reserved. [References: 15]