Bifunctional NHC‐Catalyzed Remote Enantioselective Mannich‐type Reaction of 5‐(Chloromethyl)furfural via Trienolate Intermediates

Abstract

AbstractN‐heterocyclic carbene (NHC)‐catalyzed enantioselective Mannich‐type reactions of the biomass‐derived platform compound 5‐(chloromethyl)furfural (CMF) with imines were developed. A series of high‐value‐added chiral amines were afforded in good to high yields with excellent regio‐ and enantioselectivities. The bifunctional NHC derived from ʟ‐pyroglutamic acid efficiently steered the remote addition of the trienolate intermediate to the imine in a highly stereocontrolled manner. This represents the first enantioselective reaction proceeding via an NHC‐bound trienolate intermediate.