Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls
Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually...
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sg-ntu-dr.10356-1733562024-05-17T15:31:47Z Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls Mondal, Bivas Chen, Hang Maiti, Rakesh Wang, Hongling Cai, Hui Mou, Chengli Hao, Lin Chai, Huifang Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Chemistry Ketone Atroposelective Access Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C2-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Submitted/Accepted version The authors acknowledge funding support from the National Natural Science Foundation of China (21732002, 22061007, and 22071036), the Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004], the 10 Talent Plan (Shicengci) of Guizhou Province [(2016) 5649], the Science and Technology Department of Guizhou Province [Qiankehe-jichu-ZK(2022)zhongdian024, (2018)2802, and (2019)1020], the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, the Singapore National Research Foundation under its NRF Competitive Research Program (NRF-CRP22-2019-0002), the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG70/21 and RG84/22), MOE AcRF Tier 2 (MOE2019-T2-2-117), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003), the Chair Professorship Grant, and Nanyang Technological University. 2024-01-29T08:13:51Z 2024-01-29T08:13:51Z 2023 Journal Article Mondal, B., Chen, H., Maiti, R., Wang, H., Cai, H., Mou, C., Hao, L., Chai, H. & Chi, R. Y. (2023). Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls. Organic Letters, 25(46), 8252-8257. https://dx.doi.org/10.1021/acs.orglett.3c03141 1523-7060 https://hdl.handle.net/10356/173356 10.1021/acs.orglett.3c03141 37955414 2-s2.0-85178112854 46 25 8252 8257 en NRF-CRP22-2019-0002 RG70/21 RG84/22 MOE2019-T2-2-117 MOE2018-T3-1-003 Organic Letters © 2023 American Chemical Society. All rights reserved.This article may be downloaded for personal use only. Any other use requires prior permission of the copyright holder. The Version of Record is available online at http://doi.org/10.1021/acs.orglett.3c03141. application/pdf |
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Chemistry Ketone Atroposelective Access |
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Chemistry Ketone Atroposelective Access Mondal, Bivas Chen, Hang Maiti, Rakesh Wang, Hongling Cai, Hui Mou, Chengli Hao, Lin Chai, Huifang Chi, Robin Yonggui Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| description |
Disclosed here is NHC-catalyzed direct intermolecular trapping of the ketone oxygen atom with the acyl azolium intermediate. The overall reaction is a dynamic kinetic resolution process that converts ketone to the corresponding enol ester with well-controlled axial chirality. Our reaction eventually affords non-C2-symmetric binaphthyl derivatives with important applications, such as in the area of asymmetric catalysis. |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Mondal, Bivas Chen, Hang Maiti, Rakesh Wang, Hongling Cai, Hui Mou, Chengli Hao, Lin Chai, Huifang Chi, Robin Yonggui |
| format |
Article |
| author |
Mondal, Bivas Chen, Hang Maiti, Rakesh Wang, Hongling Cai, Hui Mou, Chengli Hao, Lin Chai, Huifang Chi, Robin Yonggui |
| author_sort |
Mondal, Bivas |
| title |
Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| title_short |
Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| title_full |
Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| title_fullStr |
Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| title_full_unstemmed |
Carbene-catalyzed direct O-functionalization of ketone: atroposelective access to non-C₂-symmetric binaphthyls |
| title_sort |
carbene-catalyzed direct o-functionalization of ketone: atroposelective access to non-c₂-symmetric binaphthyls |
| publishDate |
2024 |
| url |
https://hdl.handle.net/10356/173356 |
| _version_ |
1814047146388750336 |