Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes

Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes

Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, a...

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Main Authors: Zhu, Daoyong, Jiao, Zhiwei, Chi, Robin Yonggui, Gonçalves, Théo P., Huang, Kuo-Wei, Zhou, Steve Jianrong
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2022
Subjects:
Science::Chemistry
Allylic Amination
Phosphites
Online Access:https://hdl.handle.net/10356/155084
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1550842023-02-28T19:51:47Z Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes Zhu, Daoyong Jiao, Zhiwei Chi, Robin Yonggui Gonçalves, Théo P. Huang, Kuo-Wei Zhou, Steve Jianrong School of Physical and Mathematical Sciences Science::Chemistry Allylic Amination Phosphites Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines. Agency for Science, Technology and Research (A*STAR) Economic Development Board (EDB) Accepted version We acknowledge financial support from Peking UniversityShenzhen Graduate School, Shenzhen Bay Laboratory(21230011-Scripps), Nanyang Technological University,GSK-EDB Trust Fund (2017 GSK-EDB Green and Sustain-able Manufacturing Award) and A*STAR Science andEngineering Research Council (AME IRG A1783c0010). 2022-02-08T08:12:54Z 2022-02-08T08:12:54Z 2020 Journal Article Zhu, D., Jiao, Z., Chi, R. Y., Gonçalves, T. P., Huang, K. & Zhou, S. J. (2020). Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes. Angewandte Chemie International Edition, 59(13), 5341-5345. https://dx.doi.org/10.1002/anie.201915864 1433-7851 https://hdl.handle.net/10356/155084 10.1002/anie.201915864 31965664 2-s2.0-85079427805 13 59 5341 5345 en AME IRG A1783c0010 Angewandte Chemie International Edition This is the peer reviewed version of the following article: Zhu, D., Jiao, Z., Chi, R. Y., Gonçalves, T. P., Huang, K. & Zhou, S. J. (2020). Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes. Angewandte Chemie International Edition, 59(13), 5341-5345, which has been published in final form at https://doi.org/10.1002/anie.201915864. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. application/pdf
institution Nanyang Technological University
building NTU Library
continent Asia
country Singapore
Singapore
content_provider NTU Library
collection DR-NTU
language English
topic Science::Chemistry
Allylic Amination
Phosphites
spellingShingle Science::Chemistry
Allylic Amination
Phosphites
Zhu, Daoyong
Jiao, Zhiwei
Chi, Robin Yonggui
Gonçalves, Théo P.
Huang, Kuo-Wei
Zhou, Steve Jianrong
Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
description Substituted cyclohexylamines are becoming increasingly important in drug discovery. Asymmetric Heck insertion/amination of nonconjugated cyclodienes proceeds to give 5-aryl cyclohexenylamines with good enantioselectivity and exclusive trans configurations. Primary and secondary anilines, indoline, and benzylamines are suitable amines. The weakly donating diphosphite Kelliphite forms a deep unsymmetrical pocket, which is essential for stereoselective anti attack of amines.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Zhu, Daoyong
Jiao, Zhiwei
Chi, Robin Yonggui
Gonçalves, Théo P.
Huang, Kuo-Wei
Zhou, Steve Jianrong
format Article
author Zhu, Daoyong
Jiao, Zhiwei
Chi, Robin Yonggui
Gonçalves, Théo P.
Huang, Kuo-Wei
Zhou, Steve Jianrong
author_sort Zhu, Daoyong
title Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
title_short Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
title_full Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
title_fullStr Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
title_full_unstemmed Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes
title_sort asymmetric three-component heck arylation/amination of nonconjugated cyclodienes
publishDate 2022
url https://hdl.handle.net/10356/155084
_version_ 1759858226575179776

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