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Asymmetric Synthesis of Trisubstituted Tetrahydrothiophenes via in Situ Generated Chiral Fluoride-Catalyzed Cascade Sulfa-Michael/Aldol Reaction of 1,4-Dithiane-2,5-diol and α,β-Unsaturated Ketones
A chiral fluoride-catalyzed
asymmetric cascade sulfa-Michael/aldol
condensation reaction of 1,4-dithiane-2,5-diol and a series of α,β-unsaturated
ketones is described to access chiral trisubstituted tetrahydrothiophene
derivatives. The target products, including the spiro tetrahydrothiophene
derivatives bearing a five-, six-, and seven-membered ring, were highly
functionalized and showed high ee value. This established protocol
realized a highly enantioselective reaction with a catalytic amount
of KF and Song’s chiral oligoEG via in situ generated chiral
fluoride to construct useful heterocyclic skeletons with great complexity