Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

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

doi:10.1002/anie.201915864

Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

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

Physical Sciences and Engineering

Research output: Contribution to journal › Article › peer-review

39 Scopus citations

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.

Original language	English (US)
Journal	Angewandte Chemie (International ed. in English)
DOIs	https://doi.org/10.1002/anie.201915864 https://doi.org/10.1002/ange.201915864
State	Published - Jan 22 2020

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https://repository.kaust.edu.sa/bitstream/10754/661338/1/Zhou_et_al-2020-Angewandte_Chemie_International_Edition.pdf

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title = "Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.",

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.",

author = "Zhou, {Jianrong Steve} and Daoyong Zhu and Chi, {Yonggui Robin} and Zhiwei Jiao and Theo Goncalves and Kuo-Wei Huang",

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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AU - Zhou, Jianrong Steve

AU - Zhu, Daoyong

AU - Chi, Yonggui Robin

AU - Jiao, Zhiwei

AU - Goncalves, Theo

AU - Huang, Kuo-Wei

N1 - 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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N2 - 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.

AB - 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.

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JF - Angewandte Chemie (International ed. in English)

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Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

Abstract

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CCDC 1935582: Experimental Crystal Structure Determination : 4'-bromo-N-(naphthalen-1-yl)-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-amine

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Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

Abstract

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Datasets

CCDC 1935582: Experimental Crystal Structure Determination : 4'-bromo-N-(naphthalen-1-yl)-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-amine

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