Stereoselective synthesis of protected amino alkyl epoxides

Article abstract of DOI:10.1016/S0040-4039(00)73287-4

The mechanism of epoxidation of chiral allyl amines has been investigated. The intrinsic stereoselectivity for epoxidation is shown to be approximately 5:1 and is independent of the nitrogen substituent. However, the nature of the N-protecting group influences the stability of the undesired epoxide to the acidic media, with the minor diastereomer undergoing preferential decomposition. Conditions are reported for the highly stereoselective synthesis of epoxide 9R, an important building block in the synthesis of several enzyme inhibitors.