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...
| Main Authors: | , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2022
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| Online Access: | https://hdl.handle.net/10356/155084 |
| _version_ | 1824456204949127168 |
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| author | Zhu, Daoyong Jiao, Zhiwei Chi, Robin Yonggui Gonçalves, Théo P. Huang, Kuo-Wei Zhou, Steve Jianrong |
| 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 |
| author_sort | Zhu, Daoyong |
| collection | NTU |
| 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. |
| first_indexed | 2025-02-19T03:50:24Z |
| format | Journal Article |
| id | ntu-10356/155084 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:50:24Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-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 |
| 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 |
| title | 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_short | Asymmetric three-component Heck arylation/amination of nonconjugated cyclodienes |
| title_sort | asymmetric three component heck arylation amination of nonconjugated cyclodienes |
| topic | Science::Chemistry Allylic Amination Phosphites |
| url | https://hdl.handle.net/10356/155084 |
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