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Rhodium(III)‐Catalyzed Asymmetric Access to Spirocycles through C−H Activation and Axial‐to‐Central Chirality Transfer
Author(s) -
Kong Lingheng,
Han Xi,
Liu Song,
Zou Yun,
Lan Yu,
Li Xingwei
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202000174
Subject(s) - enantioselective synthesis , chirality (physics) , rhodium , axial chirality , intramolecular force , chemistry , catalysis , allene , stereochemistry , combinatorial chemistry , organic chemistry , physics , chiral symmetry , quantum mechanics , nambu–jona lasinio model , quark
Axial‐to‐central chirality transfer is an important strategy to construct chiral centers, where the axially chiral reagents are mostly limited to atropomerically stable ones. Reported herein is a Rh III ‐catalyzed enantioselective spiroannulative synthesis of nitrones. The coupling proceeds via C−H arylation to give an atropomerically metastable biaryl, followed by intramolecular dearomative trapping under oxidative conditions with high degree of chirality transfer.