Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction
N-Heterocyclic carbene (NHC) has emerged as one of the crucial synthetic tools for asymmetric transformations of readily available materials into complex moieties. Particularly, a great deal of success has been achieved on the front of enantioselective carbon-carbon bond formation. However, in sharp...
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| Format: | Thesis-Doctor of Philosophy |
| Language: | English |
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Nanyang Technological University
2021
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| Online Access: | https://hdl.handle.net/10356/151852 |
| _version_ | 1811686525197352960 |
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| author | Rakesh, Maiti |
| author2 | Robin Yonggui Chi |
| author_facet | Robin Yonggui Chi Rakesh, Maiti |
| author_sort | Rakesh, Maiti |
| collection | NTU |
| description | N-Heterocyclic carbene (NHC) has emerged as one of the crucial synthetic tools for asymmetric transformations of readily available materials into complex moieties. Particularly, a great deal of success has been achieved on the front of enantioselective carbon-carbon bond formation. However, in sharp contrast, NHC-mediated asymmetric carbon-heteroatom bond (C-X) construction was seldomly explored. In this thesis, three novel NHC-catalyzed strategies have been developed to access C-N, C-P, and C-S bonds asymmetrically. Firstly, utilization of the NHC-bound unsaturated acyl azolium intermediate has been demonstrated to access dihydropyrimidinone scaffold (C-N bond formation) and carbon-centered chiral tertiary phosphine (C-P bond formation). In the last part, rarely explored NHC-bound alkynyl acyl azolium intermediate has been discussed and applied to obtain atroposelective axially chiral sulfone-bearing styrene derivatives (C-S bond formation). |
| first_indexed | 2024-10-01T05:01:48Z |
| format | Thesis-Doctor of Philosophy |
| id | ntu-10356/151852 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:01:48Z |
| publishDate | 2021 |
| publisher | Nanyang Technological University |
| record_format | dspace |
| spelling | ntu-10356/1518522023-02-28T23:43:24Z Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction Rakesh, Maiti Robin Yonggui Chi School of Physical and Mathematical Sciences robinchi@ntu.edu.sg Science::Chemistry N-Heterocyclic carbene (NHC) has emerged as one of the crucial synthetic tools for asymmetric transformations of readily available materials into complex moieties. Particularly, a great deal of success has been achieved on the front of enantioselective carbon-carbon bond formation. However, in sharp contrast, NHC-mediated asymmetric carbon-heteroatom bond (C-X) construction was seldomly explored. In this thesis, three novel NHC-catalyzed strategies have been developed to access C-N, C-P, and C-S bonds asymmetrically. Firstly, utilization of the NHC-bound unsaturated acyl azolium intermediate has been demonstrated to access dihydropyrimidinone scaffold (C-N bond formation) and carbon-centered chiral tertiary phosphine (C-P bond formation). In the last part, rarely explored NHC-bound alkynyl acyl azolium intermediate has been discussed and applied to obtain atroposelective axially chiral sulfone-bearing styrene derivatives (C-S bond formation). Doctor of Philosophy 2021-07-06T08:05:52Z 2021-07-06T08:05:52Z 2021 Thesis-Doctor of Philosophy Rakesh, M. (2021). Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction. Doctoral thesis, Nanyang Technological University, Singapore. https://hdl.handle.net/10356/151852 https://hdl.handle.net/10356/151852 10.32657/10356/151852 en This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License (CC BY-NC 4.0). application/pdf Nanyang Technological University |
| spellingShingle | Science::Chemistry Rakesh, Maiti Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title | Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title_full | Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title_fullStr | Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title_full_unstemmed | Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title_short | Carbene-catalyzed enantioselective carbon-heteroatom bond (C-N, C-P, C-S) construction |
| title_sort | carbene catalyzed enantioselective carbon heteroatom bond c n c p c s construction |
| topic | Science::Chemistry |
| url | https://hdl.handle.net/10356/151852 |
| work_keys_str_mv | AT rakeshmaiti carbenecatalyzedenantioselectivecarbonheteroatombondcncpcsconstruction |