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Enantioselective Construction of Vicinal Sulfur‐functionalized Quaternary and Tertiary Stereocenters via Organocatalytic Michael Addition of 5 H ‐Thiazol‐4‐ones to 1‐Azadienes
Author(s) -
Li Fushuai,
Zhang Chen,
Cheng Yuyu,
Jia Qianfa,
Li Wenjun,
Liu Kun,
Li Pengfei
Publication year - 2020
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.202000272
Subject(s) - stereocenter , enantioselective synthesis , chemistry , vicinal , phosphoric acid , sulfur , organocatalysis , michael reaction , optically active , stereochemistry , organic chemistry , catalysis
An organocatalytic enantioselective Michael addition of 5 H ‐thiazol‐4‐ones to 1‐azadienes has been developed. In the presence of chiral phosphoric acid, a series of optically active benzofuran derivatives featured by vicinal sulfur‐containing quaternary and tertiary stereocenters were obtained in high yields (71‐99%) with high stereoselectivities (70–96% ee and 8 : 1–20 : 1 d.r.).