Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system
Dual activation has become an attractive methodology in organocatalysis and has been employed as an effective strategy to achieve enantioenrich products from asymmetric catalysis. We propose an interesting mechanistic reaction, which utilized a chiral NHC-catalyst to control facial selectivity betwe...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2024
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/179539 |
| _version_ | 1826124299904221184 |
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| author | Wang, Wei Peng, Xiaolin Yang, Xiaoyan Chi, Robin Yonggui Hao, Gefei |
| author2 | School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet | School of Chemistry, Chemical Engineering and Biotechnology Wang, Wei Peng, Xiaolin Yang, Xiaoyan Chi, Robin Yonggui Hao, Gefei |
| author_sort | Wang, Wei |
| collection | NTU |
| description | Dual activation has become an attractive methodology in organocatalysis and has been employed as an effective strategy to achieve enantioenrich products from asymmetric catalysis. We propose an interesting mechanistic reaction, which utilized a chiral NHC-catalyst to control facial selectivity between NHC-bonding enolate and NHC non-covalent bonding Michael acceptor. However, the detailed effect of NHC-catalysts and the origin of chemo- and stereoselectivity still need further explanation. To illustrate the details of the mechanism, we herein employed density functional theory (DFT) to reveal the origin of chemoselectivity and stereoselectivity, which was determined by reaction kinetic control and the effect of dual activation by NHC-catalyst, respectively. We hope that this theoretical calculation could help chemists predict and design novel dual activation reactions to construct important and useful building blocks. |
| first_indexed | 2024-10-01T06:18:23Z |
| format | Journal Article |
| id | ntu-10356/179539 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:18:23Z |
| publishDate | 2024 |
| record_format | dspace |
| spelling | ntu-10356/1795392024-08-07T04:35:38Z Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system Wang, Wei Peng, Xiaolin Yang, Xiaoyan Chi, Robin Yonggui Hao, Gefei School of Chemistry, Chemical Engineering and Biotechnology Chemistry Activation effect Asymmetric catalysis Dual activation has become an attractive methodology in organocatalysis and has been employed as an effective strategy to achieve enantioenrich products from asymmetric catalysis. We propose an interesting mechanistic reaction, which utilized a chiral NHC-catalyst to control facial selectivity between NHC-bonding enolate and NHC non-covalent bonding Michael acceptor. However, the detailed effect of NHC-catalysts and the origin of chemo- and stereoselectivity still need further explanation. To illustrate the details of the mechanism, we herein employed density functional theory (DFT) to reveal the origin of chemoselectivity and stereoselectivity, which was determined by reaction kinetic control and the effect of dual activation by NHC-catalyst, respectively. We hope that this theoretical calculation could help chemists predict and design novel dual activation reactions to construct important and useful building blocks. We acknowledge financial support from the National Key R&D Program of China (2021YFD1700100); The Central Government Guides Local Science and Technology Development Fund Projects (Qiankehezhongyindi (2023) 001); The Program of High-level Innovation Talents, Guizhou Province, China (Qiankehepingtairencai-GCC (2023) 044); and The Program of Major Scientific and Technological, Guizhou Province, China (Qiankehechengguo (2024) zhongda007). 2024-08-07T04:35:38Z 2024-08-07T04:35:38Z 2024 Journal Article Wang, W., Peng, X., Yang, X., Chi, R. Y. & Hao, G. (2024). Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system. Organic Chemistry Frontiers, 11(14), 3929-3938. https://dx.doi.org/10.1039/d4qo00660g 2052-4129 https://hdl.handle.net/10356/179539 10.1039/d4qo00660g 2-s2.0-85194909800 14 11 3929 3938 en Organic Chemistry Frontiers © The Author(s). All rights reserved. |
| spellingShingle | Chemistry Activation effect Asymmetric catalysis Wang, Wei Peng, Xiaolin Yang, Xiaoyan Chi, Robin Yonggui Hao, Gefei Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title | Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title_full | Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title_fullStr | Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title_full_unstemmed | Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title_short | Unveiling the dual activation effect of NHC-catalyst in an asymmetric reaction system |
| title_sort | unveiling the dual activation effect of nhc catalyst in an asymmetric reaction system |
| topic | Chemistry Activation effect Asymmetric catalysis |
| url | https://hdl.handle.net/10356/179539 |
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