Reductive alkylation of beta-alkoxy aziridines: new route to substituted allylic amines.

[reaction: see text] A new route to substituted cyclic allylic amines via the reductive alkylation of beta-alkoxy aziridines using excess alkyllithium reagents is described.

cis- and trans-stereoselective epoxidation of N-protected 2-cyclohexen-1-ylamines.

The first systematic study of the cis and trans stereoselectivity in the m-CPBA epoxidation of N-protected cyclic allylic amines has been completed. Mono-N-protected systems gave epoxides with cis stereochemistry (amides are better cis directors than sulfonamides or carbamates) whereas di-N-protected systems gave trans-epoxides (TsNBoc protection gave complete trans stereoselectivity). [structure: see text]