Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts
An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-al...
| 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/10356/155454 |
| _version_ | 1811683764263190528 |
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| author | Pal, Kumar Bhaskar Lee, Jiande Das, Mrinmoy Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Pal, Kumar Bhaskar Lee, Jiande Das, Mrinmoy Liu, Xue-Wei |
| author_sort | Pal, Kumar Bhaskar |
| collection | NTU |
| description | An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity. |
| first_indexed | 2024-10-01T04:17:55Z |
| format | Journal Article |
| id | ntu-10356/155454 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:17:55Z |
| publishDate | 2022 |
| record_format | dspace |
| spelling | ntu-10356/1554542022-03-17T03:01:57Z Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts Pal, Kumar Bhaskar Lee, Jiande Das, Mrinmoy Liu, Xue-Wei School of Physical and Mathematical Sciences Nanyang Environment and Water Research Institute Science::Chemistry C-glycosylation Stereoselectivity An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity. Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) We thank Nanyang Technological University (RG120/18) and the Ministry of Education (MOE 2013-T3-1-002) and National Research Foundation (NRF2016NRF-NSFC002-005), Singapore, for their financial support. 2022-03-17T03:01:57Z 2022-03-17T03:01:57Z 2020 Journal Article Pal, K. B., Lee, J., Das, M. & Liu, X. (2020). Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts. Organic and Biomolecular Chemistry, 18(12), 2242-2251. https://dx.doi.org/10.1039/d0ob00247j 1477-0520 https://hdl.handle.net/10356/155454 10.1039/d0ob00247j 32159571 2-s2.0-85082395881 12 18 2242 2251 en RG120/18 MOE2013- T3-1-002 NRF2016NRF-NSFC002-005 Organic and Biomolecular Chemistry © The Royal Society of Chemistry 2020. All rights reserved. |
| spellingShingle | Science::Chemistry C-glycosylation Stereoselectivity Pal, Kumar Bhaskar Lee, Jiande Das, Mrinmoy Liu, Xue-Wei Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title | Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title_full | Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title_fullStr | Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title_full_unstemmed | Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title_short | Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts |
| title_sort | palladium ii catalyzed stereoselective synthesis of c glycosides from glycals with diaryliodonium salts |
| topic | Science::Chemistry C-glycosylation Stereoselectivity |
| url | https://hdl.handle.net/10356/155454 |
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