Enantioselective synthesis of axially chiral vinyl arenes through palladium-catalyzed C-H olefination

A palladium-catalyzed ketoxime-chelation-assisted enantioselective C-H olefination of 2-arylcyclohex-2-enone oxime ether with a wide range of olefins as coupling partners was developed. Employing ketoxime ether as an efficient directing group, a variety of axially chiral vinyl arenes was synthesized...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2018, Vol.54 (76), p.176-179
Main Authors: Sun, Qiao-Ying, Ma, Wei-Yang, Yang, Ke-Fang, Cao, Jian, Zheng, Zhan-Jiang, Xu, Zheng, Cui, Yu-Ming, Xu, Li-Wen
Format: Article
Language:English
Subjects:
Alkenes
Aromatic compounds
Chelation
Chemical synthesis
Crystallography
Enantiomers
Palladium
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Summary:A palladium-catalyzed ketoxime-chelation-assisted enantioselective C-H olefination of 2-arylcyclohex-2-enone oxime ether with a wide range of olefins as coupling partners was developed. Employing ketoxime ether as an efficient directing group, a variety of axially chiral vinyl arenes was synthesized by Pd( ii )-catalyzed C-H functionalization with excellent enantioselectivities (96 → 99% ee) under mild conditions. A palladium-catalyzed ketoxime-chelation-assisted C-H olefination was developed to afford axially chiral vinyl arenes with excellent enantioselectivities.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc05555f