Remote asymmetric induction in lewis acid-catalyzed Diels-Alder reaction of α,β-unsaturated enones having a chiral sulfinyl-substituted, 5-membered aromatic heterocycle

Article abstract of DOI:10.1248/cpb.46.1078

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%.