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

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

5 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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CCDC 1935582: Experimental Crystal Structure Determination : 4'-bromo-N-(naphthalen-1-yl)-1,2,3,6-tetrahydro[1,1'-biphenyl]-3-amine
Zhou, J. S. (Creator), Zhu, D. (Creator), Chi, Y. R. (Creator), Jiao, Z. (Creator), Goncalves, T. (Creator), Huang, K. (Creator), Zhou, J. S. (Creator), Zhu, D. (Creator), Chi, Y. R. (Creator) & Jiao, Z. (Creator), Cambridge Crystallographic Data Centre, Feb 13 2020
DOI: 10.5517/ccdc.csd.cc22z44c, http://hdl.handle.net/10754/664841
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@article{e7bcde2df7aa42aa89e5664e8a7777b7,

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).",

year = "2020",

month = jan,

day = "22",

doi = "10.1002/anie.201915864",

language = "English (US)",

journal = "Angewandte Chemie (International ed. in English)",

issn = "1433-7851",

publisher = "Wiley",

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T1 - Asymmetric Three-Component Heck/Amination of Nonconjugated Cyclodienes.

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).

PY - 2020/1/22

Y1 - 2020/1/22

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.

UR - http://hdl.handle.net/10754/661338

UR - http://doi.wiley.com/10.1002/anie.201915864

UR - http://www.scopus.com/inward/record.url?scp=85079427805&partnerID=8YFLogxK

U2 - 10.1002/anie.201915864

DO - 10.1002/anie.201915864

M3 - Article

C2 - 31965664

JO - Angewandte Chemie (International ed. in English)

JF - Angewandte Chemie (International ed. in English)

SN - 1433-7851

ER -

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

Cite this