Catalytic enantioselective construction of all-carbon quaternary stereocenters by an organocatalytic Diels–Alder reaction of α-substituted α,β-unsaturated aldehydes

Abstract

A binaphthyl-based primary amine (R)-3d was designed for the Diels–Alder reaction of α-substituted α,β-unsaturated aldehydes; in the presence of the TfOH salt of (R)-3d, the Diels–Alder reaction of α-substituted α,β-unsaturated aldehydes with cyclopentadiene proceeded to afford the corresponding cycloadducts having one all-carbon quaternary stereocenter in good yield with good to high stereoselectivity.