4.8 Article

Hydrogen-Bond-Mediated Cascade Reaction Involving Chalcones: Facile Synthesis of Enantioenriched Trisubstituted Tetrahydrothiophenes

Journal

ORGANIC LETTERS
Volume 14, Issue 4, Pages 1090-1093

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol2034959

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A bifunctional squaramide catalyzed sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and chalcones with a low catalyst loading has been developed. Trisubstituted tetrahydrothiophenes with three contiguous stereogenic centers are obtained in a highly stereocontrolled manner. Additionally, a remarkable temperature effect on reaction efficiency was observed and a synthetically potential gram-synthesis was also conducted.

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