N-Heterocyclic carbene catalyzed desymmetrization of diols: access to enantioenriched oxindoles having a C3-quaternary stereocenter

Abstract

Herein, we describe an effective strategy for enantioselective synthesis of oxindoles having a C3-quaternary stereocenter via N-heterocyclic carbene (NHC) catalyzed desymmetrization of diols. The process is based on the catalytic asymmetric transfer acylation of primary alcohols using readily available aldehydes as an acylation agent. The reaction enables easy access to diversely functionalized C3-quaternary oxindoles with excellent enantioselectivity. The synthetic potential of the process is further demonstrated via the preparation of the key intermediate for (−)-esermethole and (−)-physostigmine.