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