Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions
A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation o...
| Main Authors: | , , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Subjects: | |
| Online Access: | https://hdl.handle.net/10356/137777 |
| _version_ | 1811684043220058112 |
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| author | Wang, Hongling Wang, Yuhuang Chen, Xingkuan Mou, Chengli Yu, Shuyan Chai, Huifang Jin, Zhichao Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Wang, Hongling Wang, Yuhuang Chen, Xingkuan Mou, Chengli Yu, Shuyan Chai, Huifang Jin, Zhichao Chi, Robin Yonggui |
| author_sort | Wang, Hongling |
| collection | NTU |
| description | A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions. |
| first_indexed | 2024-10-01T04:22:21Z |
| format | Journal Article |
| id | ntu-10356/137777 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:22:21Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1377772023-02-28T19:46:46Z Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions Wang, Hongling Wang, Yuhuang Chen, Xingkuan Mou, Chengli Yu, Shuyan Chai, Huifang Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Enantioselective Chirality A new class of chiral oxidants is developed. These readily accessible oxidants contain a nitro group for oxidation and a chiral sulfonamide moiety for stereoselectivity control. The chiral information from the oxidants can effectively transfer to the substrates in carbene-catalyzed β-hydroxylation of enals via single-electron-transfer radical processes. We expect these oxidants to find unique applications in other asymmetric oxidations and oxygen-atom-transferring reactions. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-14T06:45:30Z 2020-04-14T06:45:30Z 2019 Journal Article Wang, H., Wang, Y., Chen, X., Mou, C., Yu, S., Chai, H., ... , Chi, R. Y. (2019). Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions. Organic Letters, 21(18), 7440-7444. doi:10.1021/acs.orglett.9b02736 1523-7060 https://hdl.handle.net/10356/137777 10.1021/acs.orglett.9b02736 31478384 2-s2.0-85072546160 18 21 7440 7444 en Organic Letters This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b02736 application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry Enantioselective Chirality Wang, Hongling Wang, Yuhuang Chen, Xingkuan Mou, Chengli Yu, Shuyan Chai, Huifang Jin, Zhichao Chi, Robin Yonggui Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title | Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title_full | Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title_fullStr | Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title_full_unstemmed | Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title_short | Chiral nitroarenes as enantioselective single-electron-transfer oxidants for carbene-catalyzed radical reactions |
| title_sort | chiral nitroarenes as enantioselective single electron transfer oxidants for carbene catalyzed radical reactions |
| topic | Science::Chemistry::Organic chemistry Enantioselective Chirality |
| url | https://hdl.handle.net/10356/137777 |
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