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Enantioselective Oxidative Gold Catalysis Enabled by a Designed Chiral P,N‐Bidentate Ligand
Author(s) -
Ji Kegong,
Zheng Zhitong,
Wang Zhixun,
Zhang Liming
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201409300
Subject(s) - cyclopropanation , enantioselective synthesis , carbene , denticity , chemistry , ligand (biochemistry) , moiety , intramolecular force , piperidine , stereochemistry , combinatorial chemistry , oxidative addition , catalysis , organic chemistry , metal , receptor , biochemistry
A newly developed P,N‐bidentate ligand enables enantioselective intramolecular cyclopropanation by a reactive α‐oxo gold carbene intermediate generated in situ. The ligand design is based on our previously proposed structure (with a well‐organized triscoordinated gold center) of the carbene intermediate in the presence of a P,N‐bidentate ligand. A C 2 ‐symmetric piperidine ring was incorporated in the ligand as the nitrogen‐containing moiety. A range of racemic transformations of α‐oxo gold carbene intermediates have been developed recently, and this new class of chiral ligands could enable their modification for asymmetric synthesis, as demonstrated in this study.