Organocatalytic Enantioselective Domino Michael-aldol Condensation of 5-Oxoalkanal and α,β-Unsaturated Aldehydes. Efficient Assembly of Densely Functionalized Cyclohexenes

Abstract

Organocatalytic Michael reaction of glutaraldehyde and 3-arylpropenal followed by the subsequent intramolecular aldol condensation provided 2-arylcyclohex-3-ene-1,3-dicarbaldehydes. Reactions with the 5-oxohexanal variant afforded the highly functionalized cyclohexenedicarbaldehydes in high diastereoselectivity and high enantioselectivity (>99% ee). Structure of the adduct 3j was confirmed unambiguously by X-ray analysis.