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Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

ABSTRACT: A newly developed P,N-bidentate ligand enables enantioselective intramolecular cyclopropanation by a reactive ?-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 C2-symmetric piperidine ring was incorporated in the ligand as the nitrogen-containing moiety. A range of racemic transformations of ?-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.

SUBMITTER: Ji K

PROVIDER: S-EPMC4300284 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Enantioselective oxidative gold catalysis enabled by a designed chiral P,N-bidentate ligand.

Ji Kegong K Zheng Zhitong Z Wang Zhixun Z Zhang Liming L

Angewandte Chemie (International ed. in English) 20141127 4

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 C2-symmetric piperidine ring was incorporated in the ligand as the nitrogen-containing moiety. A range of racemic transformations of α-oxo gold carben ...[more]

PMID: 25431180

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