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Phosphoric Acid Catalyzed Asymmetric 1,6‐Conjugate Addition of Thioacetic Acid to para ‐Quinone Methides
Author(s) -
Dong Nan,
Zhang ZhiPei,
Xue XiaoSong,
Li Xin,
Cheng JinPei
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201509110
Subject(s) - phosphoric acid , conjugate , catalysis , chemistry , quinone , enantioselective synthesis , organic chemistry , sulfur , combinatorial chemistry , mathematical analysis , mathematics
An asymmetric 1,6‐conjugate addition of thioacetic acid with para ‐quinone methides has been developed by using chiral phosphoric acid catalysis in the presence of water. A series of sulfur‐containing compounds were thus obtained in high yields with good to excellent enantioselectivities. Theoretical studies indicated that the water‐bridged proton transfer is a potentially favorable reaction pathway. An unprecedented O−H⋅⋅⋅π interaction between water and the aromatic nucleus of chiral phosphoric acid was discovered to contribute significantly to the stereocontrol in the catalysis.