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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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201811621
Subject(s) - enantioselective synthesis , stereocenter , chemistry , diastereomer , sulfide , catalysis , amine gas treating , organic chemistry , aryl , combinatorial chemistry , 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.