Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 5, Pages 1315-1319Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201811621
Keywords
chlorination; cyclizations; Lewis base catalysis; olefins; synthetic methods
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Funding
- One Thousand Youth Talents Program of China
- National Natural Science Foundation of China [21772239]
- Natural Science Foundation of Guangdong Province [2014A030312018]
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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.
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