Asymmetric base-mediated epoxide isomerisation.
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.
Magnus
Angelika
A
Department of Organic Chemistry, Institute of Chemistry, Uppsala University, Box 531, S-751 21 Uppsala, Sweden.
Bertilsson
Sophie K
SK
Andersson
Pher G
PG