Remote Asymmetric Induction in Lewis Acid-Catalyzed Diels-Alder Reaction of α, β-Unsaturated Enones Having a Chiral Sulfinyl-Substituted, 5-Membered Aromatic Heterocycle

Abstract

Two types of chiral sulfoxides as Diels-Alder dienophiles were synthesized and high levels of diastereoselectivity were observed in cycloadditions. 2-Furyl and 2-thienyl α, β-enones, bearing a chiral sulfinyl group in the heterocycle, served as efficient dienophiles in Diels-Alder reactions, where the catalytic use of aluminium chloride or a lanthanide triflate effected the cycloaddition with cyclopentadiene affording the endo adduct with high diastereoselectivity, ranging from 91% to 98%.