Application of New Camphor-Derived Mercapto Chiral Auxiliaries to the Synthesis of Optically Active Primary Amines

Article abstract of DOI:10.1021/jo00083a037

A series enantiomerically pure sulfinimines carrying new camphor-based mercapto chiral auxiliaries are subjected to assymetric 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.