4.8 Review

Asymmetric base-mediated epoxide isomerisation

Journal

CHEMICAL SOCIETY REVIEWS
Volume 31, Issue 4, Pages 223-229

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b104372m

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The base-mediated rearrangement of epoxides into allylic : alcohols is a well-known synthetic transformation. The first enantioselective version of the reaction-using a chiral base was reported in 1980. Since then, the reaction: has received a lot of attention mostly due to the great usefulness of chiral. allylic alcohols in organic synthesis. Major breakthroughs in the area were the first report on using a sub-stoichiometric amount of chiral:base, and the development of chiral bases for a true catalytic reaction protocol. The present review covers the time from when. the first asymmetric epoxide isomerisation. reaction was reported (1980) up to now, focusing on the period 1997-2001.

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