Trienamine Catalysis with 2,4‐Dienones: Development and Application in Asymmetric Diels–Alder Reactions

Abstract

A tri-ing reaction: An asymmetric Diels–Alder cycloaddition of δ,δ-disubstituted 2,4-dienones is possible through the trienamine catalysis of cinchona-based primary amines (see scheme). An array of electron-deficient dienophiles, such as N-substituted maleimides and 3-alkenyl oxindoles, were tolerated, and multifunctional cyclohexene derivatives were obtained in excellent stereoselectivity and with high diastereomer ratios.