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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

Author:
Duan, Mengying, Liu, Yidong, Ao, Jun, Xue, Lu, Luo, Shilong, Tan, Yu, Qin, Wenling, Song, Choong Eui, Yan, Hailong
Source:
Organic letters 2017 v.19 no.9 pp. 2298-2301
ISSN:
1523-7052
Subject:
chemical structure, condensation reactions, enantioselectivity, fluorides, heterocyclic compounds, ketones
Abstract:
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.
Agid:
5794037