Direct enantio- and diastereoselective Mannich reactions of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine

Abstract

A highly diastereo- and enantioselective Mannich reaction of isatin-derived ketimines with oxo-indanecarboxylates catalyzed by chiral thiourea derived from hydroquinidine has been developed. A series of 3-substituted 3-amino-oxindoles containing assembled bicyclic rings linked by a C–C bond were constructed by this protocol in excellent yields (92–99%) with high enantioselectivities (85–99% ee) and diastereoselectivities (up to >99 : 1 dr).