Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement
A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the invo...
| Main Authors: | , , , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
| Published: |
2020
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| Online Access: | https://hdl.handle.net/10356/144929 |
| _version_ | 1811687668042432512 |
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| author | Huang, Nianyu Liao, Hongze Yao, Hui Xie, Tianpeng Zhang, Shasha Zou, Kun Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Huang, Nianyu Liao, Hongze Yao, Hui Xie, Tianpeng Zhang, Shasha Zou, Kun Liu, Xue-Wei |
| author_sort | Huang, Nianyu |
| collection | NTU |
| description | A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement of allenic ester as the glycosyl acceptor. A wide range of substrate scope with good to excellent yields was achieved with complete diastereoselectivity. |
| first_indexed | 2024-10-01T05:19:58Z |
| format | Journal Article |
| id | ntu-10356/144929 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T05:19:58Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1449292023-02-28T19:49:44Z Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement Huang, Nianyu Liao, Hongze Yao, Hui Xie, Tianpeng Zhang, Shasha Zou, Kun Liu, Xue-Wei School of Physical and Mathematical Sciences Science::Chemistry Catalysts Chemical Reactions A novel gold-catalyzed C-glycosylation has been developed to gain access to α,(Z)-selective C-vinyl glycosides, starting from readily available glycals and propargylic carboxylate. This reaction involves a tandem intermolecular gold-catalyzed 1,3-acyloxy migration/Ferrier rearrangement with the involvement of allenic ester as the glycosyl acceptor. A wide range of substrate scope with good to excellent yields was achieved with complete diastereoselectivity. Ministry of Education (MOE) National Research Foundation (NRF) Accepted version We thank the Ministry of Education (MOE 2013-T3-1-002), National Research Foundation (NRF2016NRF-NSFC002-005), Nanyang Technological University, Singapore (RG14/16), China Scholarship Council (No. 201508420062), and Youth Talent Development Foundation of China Three Gorges University for their financial support. Dr. Yongxin Li and Dr. Ganguly Rakesh in the division of chemistry and biological chemistry, Nanyang Technological University are also acknowl-edged for X-ray analysis. 2020-12-03T06:36:04Z 2020-12-03T06:36:04Z 2017 Journal Article Huang, N., Liao, H., Yao, H., Xie, T., Zhang, S., Zou, K., & Liu, X.-W. (2018). Diastereoselective synthesis of C-vinyl glycosides via gold(i)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement. Organic Letters, 20(1), 16-19. doi:10.1021/acs.orglett.7b03062 1523-7060 https://hdl.handle.net/10356/144929 10.1021/acs.orglett.7b03062 1 20 16 19 en NRF2016NRF-NSFC002-005 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.7b03062 application/pdf |
| spellingShingle | Science::Chemistry Catalysts Chemical Reactions Huang, Nianyu Liao, Hongze Yao, Hui Xie, Tianpeng Zhang, Shasha Zou, Kun Liu, Xue-Wei Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title | Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title_full | Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title_fullStr | Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title_full_unstemmed | Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title_short | Diastereoselective synthesis of C‑vinyl glycosides via gold(I)-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement |
| title_sort | diastereoselective synthesis of c vinyl glycosides via gold i catalyzed tandem 1 3 acyloxy migration ferrier rearrangement |
| topic | Science::Chemistry Catalysts Chemical Reactions |
| url | https://hdl.handle.net/10356/144929 |
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