APPLICATION OF NEW CAMPHOR-DERIVED MERCAPTO CHIRAL AUXILIARIES TO THE SYNTHESIS OF OPTICALLY-ACTIVE PRIMARY AMINES

A series of enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to asymmetric alkylation. Such reaction offers an excellent route to the preparation of optically active primary amines. Also reported here is an unprecedented Grignard addition of a chiral sulfenimine leading to a single enantiomer of the corresponding sulfenamide and thence produced enantiopure amine after acidic aqueous workup. The chiral auxiliary can be recovered in high yield.