COAP/Pd-catalyzed asymmetric linear allylic alkylation for synthesizing chiral 3,3′-disubstituted oxindoles bearing all-carbon quaternary stereocenters and primary allylic alcohol structures

Abstract

A linear asymmetric allylic alkylation of 3-aryl oxindole derivatives with vinyloxirane was reported by using a chiral oxalamide–phosphine (COAP)/Pd(0) complex as a catalyst, which provided chiral 3,3′-oxindole derivatives containing all-carbon quaternary stereocenters and an allylic alcohol side chain in good yields with excellent regio- and enantioselectivity (up to 92% yield and 98% ee). The developed protocol provided a straightforward synthetic route with broad functional group tolerance under mild, base-free reaction conditions.