Regio- and stereoselective synthesis of aziridino epoxides from cyclic dienes

Abstract

Two different routes for the regio- and stereoslective synthesis of aziridino epoxides from cyclic dienes have been explored. The first strategy involves regiospecific aziridination of cyclic diene derivatives and subsequent epoxidation with m-CPBA to yield cis-aziridino epoxides as major products. The second strategy utilizes regiospecific epoxidation of cyclic diene derivatives followed by Sharpless aziridination to provide exclusively trans-aziridino epoxides. Synthesis of both enantiomers of cis-aziridino epoxides from (R)-(-)- and (S)-(+)-carvones are also reported.