Bifunctional NHC‐Catalyzed Remote Enantioselective Mannich‐type Reaction of 5‐(Chloromethyl)furfural via Trienolate Intermediates
Yuan‐Yuan Gao, Chunlin Zhang, Ming‐Lei Jin, Zhong‐Hua Gao, Song Ye
Abstract
N-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.
Topics & Concepts
Enantioselective synthesisBifunctionalCarbeneChemistryFurfuralCatalysisImineMannich reactionOrganic chemistryCombinatorial chemistryN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthetic Organic Chemistry MethodsAsymmetric Hydrogenation and Catalysis