Palladium(ii) complex-catalysed enantioselective benzoylation of alcohols using carbon monoxide and an organobismuth(v) compound

Abstract

A novel method for the kinetic resolution of racemic secondary alcohols via their enantioselective benzoylation has been explored using CO, Ph₃Bi(OAc)₂, a catalytic amount of a chiral Pd(II) complex and AgOAc. In this catalytic system, Ph₃Bi(OAc)₂ has been revealed to work better than any other phenylating reagents such as PhB(OH)₂ or PhSnMe₃. It has also been disclosed that the planar chirality of optically active oxazolinylferrocenylphosphine (3e) has some positive effect on the enantioselectivity. Satisfactory enantioselectivity has not yet been obtained (up to 48% ee), but this reaction system seems to be interesting from the viewpoint of both asymmetric synthesis and organobismuth chemistry.