Highly selective aziridination of imines using trimethylsilyldiazomethane and applications of C-silylaziridines in synthesis

Trimethylsilyldiazomethane has been found to add directly to N-sulfonyl (Ts and SES) imines to afford aziridines in good yields and high cis stereoselectivities. The silyl group can be substituted by treatment with a fluoride source and electrophiles again with high selectivity. Complete regioselectivity is observed in ring opening of these aziridines with nucleophiles.