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Chiral Sulfide Catalysis for Desymmetrizing Enantioselective Chlorination
Author(s) -
Cao Qingxiang,
Luo Jie,
Zhao Xiaodan
Publication year - 2019
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.201811621
Subject(s) - enantioselective synthesis , stereocenter , diastereomer , chemistry , sulfide , catalysis , organic chemistry , amine gas treating , aryl , alkyl
An unprecendented chiral sulfide catalyzed desymmetrizing enantioselective chlorination is disclosed. Various aryl‐tethered diolefins and diaryl‐tethered olefins afforded teralins and tricyclic hexahydrophenalene derivatives, respectively, bearing multiple stereogenic centers in high yields with excellent enantio‐ and diastereoselectivities. In contrast, the tertiary amine catalyst (DHQD) 2 PHAL led to a diastereomeric product. The products could be transformed into a variety of compounds, such as spiro‐N‐heterocycles.