Regio- and Stereoselective Synthesis of Aziridino Epoxides from Cyclic Dienes

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.