Enzymatic dynamic kinetic resolution of (±)-cis-N-(Alkoxycarbonyl) cyclopentane-1,2-diamines based on spontaneous racemization

摘要

Lipase B from Candida antarctica is an excellent catalyst for the enantioselective acetylation of different (±)-cis-N-(alkoxycarbonyl) cyclopentane-1,2-diamines. Depending on the alkoxycarbonyl group, a simple kinetic resolution (Boc-derivative) or an interesting dynamic kinetic resolution (DKR with Cbz-, Alloc, and ethoxycarbonyl derivatives) has been developed. Racemization for the DKR occurred due to the N,N′ intramolecular migration of the alkoxycarbonyl group.