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

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