ELECTROPHILIC AMINATION - PREPARATION AND USE OF N-BOC-3-(4-CYANOPHENYL)OXAZIRIDINE, A NEW REAGENT THAT TRANSFERS A N-BOC GROUP TO N-NUCLEOPHILES AND C-NUCLEOPHILES

We describe the preparation of the title compound 2b via aza-Wittig re action of N-Boc-triphenyliminophosphorane (6) with 4-cyanobenzaldehyde followed by Oxone oxidation of the resulting imine 5b. Oxaziridine 2b is a stable, crystalline solid, which transfers under mild conditions its N-Boc fragment to primary and secondary amines (to give N(beta)-B oc-hydrazines) and enolates (to give N-Boc-amino derivatives).