NHC-Catalyzed Chemoselective Reactions of Enals and Cyclopropylcarbaldehydes for Access to Chiral Dihydropyranone Derivatives.

Abstract

An N-heterocyclic carbene (NHC)-catalyzed chemoselective activation reaction of 1-cyclopropylcarbaldehydes and α-alkynyl enals is reported. NHC selectively catalyzes 1-cyclopropylaldehydes, followed by a [2 + 4] cycloaddition reaction with α-alkynyl enals. The target dihydropyranone derivatives bearing different substituents and substitution patterns can be obtained in good to excellent yields with excellent enantio- and diastereoselectivities under mild conditions.