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An Organocatalytic Domino Thia‐Michael/Aldol Condensation Reaction: Highly Enantioselective Synthesis of Functionalized Dihydrothiophenes
Author(s) -
Tang Jie,
Xu Dan Qian,
Xia Ai Bao,
Wang Yi Feng,
Jiang Jun Rong,
Luo Shu Ping,
Xu Zhen Yuan
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000245
Subject(s) - domino , chemistry , aldol reaction , michael reaction , enantioselective synthesis , aldol condensation , organocatalysis , cascade reaction , catalysis , organic chemistry , combinatorial chemistry
An organocatalytic domino thia‐Michael/aldol condensation reaction of α, β‐unsaturated aldehydes with 1, 4‐dithiane‐2,5‐diol catalyzed by chiral diphenylprolinol TMS ether has been developed, which provides a new practical and direct route to chiral dihydrothiophenes with high yields (up to 90%) and excellent enantioselectivities (up to>99% ee ). The catalytic mechanism of the domino reaction was further confirmed through the APCI‐MS detection of proposed reaction intermediates.