Hydrogen-bond-mediated cascade reaction involving chalcones: facile synthesis of enantioenriched trisubstituted tetrahydrothiophenes |
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Authors: | Ling Jun-Bing Su Yu Zhu Hai-Liang Wang Guan-Yu Xu Peng-Fei |
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Institution: | State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, P. R. China. |
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Abstract: | 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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