Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

Jianrong Steve Zhou, Daoyong Zhu, Yonggui Robin Chi, Zhiwei Jiao, Theo Goncalves, Kuo-Wei Huang

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Abstract

Asymmetric Heck/amination of nonconjugated cyclodienes proceeds to give substituted cyclohexenylamines in good enantioselectivity and exclusive trans configurations. Substituted chiral cyclohexylamines are becoming increasingly important in drug discovery. Suitable amines in this reaction include primary and secondary anilines, indoline and benzylamines. A weakly-donating diphosphite, Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti-attack of external amines.

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We acknowledge financial support from Peking University Shenzhen Graduate School, Shenzhen Bay Laboratory(21230011-Scripps), Nanyang Technological University, GSK-EDB Trust Fund (2017 GSK-EDB Green andSustainable Manufacturing Award) and A*STAR Science andEngineering Research Council (AME IRG A1783c0010).

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