Catalytic Enantioselective Construction of Chiral Benzo-Fused N-Heterocycles through Friedel-Crafts-Type Electrophilic Chlorination
Congratulations! The publication of our group in CCS Chem., "Catalytic Enantioselective Construction of Chiral Benzo-Fused N-Heterocycles through Friedel-Crafts-Type Electrophilic Chlorination" has been published recently (Jie Luo, Yuanyuan Zhang, Fuming Zhong, and Xiaodan Zhao*CCS Chem., 2021, 3, 1363–1375).
Chiral benzo-fused N-heterocycles are frequently found in natural and synthetic products. However, their synthesis usually suffers from different limitations such as hard accessibility of appropriate starting materials and unsatisfactory stereoselectivities. In this work, an unprecedented chiral sulfide-catalyzed enantioselective Friedel-Crafts-type electrophilic chlorination is disclosed to construct various 3,4-functionalized tetrahydroquinolines with excellent enantio- and diastereoselectivities from easily available aniline derivatives. Interestingly, employing N-allyl 1-naphthanilides as substrates, divergent reactions via chlorocarbocyclization and dearomatization occurred to afford two chiral polycyclic benzo-fused N-heterocycles. The developed system extends the scope of asymmetric chlorination to general substrates without the need of N-H group, and significantly promotes the synthesis of enantioenriched benzo-fused N-heterocycles.
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