Catalytic asymmetric acylation of racemic secondary alcohols with benzoyl chloride in the presence of a chiral diamine

Nonenzymatic kinetic resolution of racemic secondary alcohols is an efficie nt synthetic method to obtain optically active compounds in organic chemist ry. Catalytic asymmetric acylation of racemic secondary alcohols has been s uccessfully performed with achiral benzoyl chloride in the presence of only 0.3 mol% of chiral diamine (3) derived from (S)-proline, combined with 0.5 equivalent of triethylamine. This asymmetric acylation of various racemic cyclic secondary alcohols, 5, 6, or 8 membered cycloalkanols (la-lc), hydro xyesters (Id and le), and bromohydrins (If and Ig) gave the corresponding o ptically active benzoates (84-97% ee) and unreacted alcohols (79-95% ee). R acemic acyclic secondary alcohols (1h-1j) were also acylated in moderate en antioselectivity.