Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates
A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between a,b-unsaturated aldehydes and a-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups,...
| 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/10356/138269 |
| _version_ | 1826117213666410496 |
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| author | Sun, Jun He, Fangcheng Wang, Zhongyao Pan, Dingwu Zheng, Pengcheng Mou, Chengli Jin, Zhichao Chi, Robin Yonggui |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Sun, Jun He, Fangcheng Wang, Zhongyao Pan, Dingwu Zheng, Pengcheng Mou, Chengli Jin, Zhichao Chi, Robin Yonggui |
| author_sort | Sun, Jun |
| collection | NTU |
| description | A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between a,b-unsaturated aldehydes and a-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities.
Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection. |
| first_indexed | 2024-10-01T04:23:58Z |
| format | Journal Article |
| id | ntu-10356/138269 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T04:23:58Z |
| publishDate | 2020 |
| record_format | dspace |
| spelling | ntu-10356/1382692023-02-28T19:25:41Z Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates Sun, Jun He, Fangcheng Wang, Zhongyao Pan, Dingwu Zheng, Pengcheng Mou, Chengli Jin, Zhichao Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry NHC Catalyst Enantioselectivities A carbene-catalyzed enantioselective [4+2] cycloaddition reaction between a,b-unsaturated aldehydes and a-ketophosphonates is developed. The reaction affords chiral 2-pyranylphosphonates with excellent enantioselectivities. The optically enriched phosphonate products bear multiple functional groups, including unsaturated lactone and phosphonate moieties that often lead to unique bio-activities. Preliminary studies show that the products from our reactions exhibit anti-bacterial (X. oryzae pv. oryzae) and anti-viral (Tobacco Mosaic Virus) activities for potential use in plant protection. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-30T01:58:49Z 2020-04-30T01:58:49Z 2018 Journal Article Sun, J., He, F., Wang, Z., Pan, D., Zheng, P., Mou, C., . . ., Chi, R. Y. (2018). Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates. Chemical Communications, 54(47), 6040-6043. doi:10.1039/C8CC03017K 1359-7345 https://hdl.handle.net/10356/138269 10.1039/C8CC03017K 47 54 6040 6043 en Chemical Communications © 2018 The Royal Society of Chemistry. All rights reserved. This paper was published in Chemical Communications and is made available with permission of The Royal Society of Chemistry. application/pdf |
| spellingShingle | Science::Chemistry::Organic chemistry NHC Catalyst Enantioselectivities Sun, Jun He, Fangcheng Wang, Zhongyao Pan, Dingwu Zheng, Pengcheng Mou, Chengli Jin, Zhichao Chi, Robin Yonggui Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title | Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title_full | Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title_fullStr | Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title_full_unstemmed | Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title_short | Carbene-catalyzed enal γ-carbon addition to α-ketophosphonates for enantioselective access to bioactive 2-pyranylphosphonates |
| title_sort | carbene catalyzed enal γ carbon addition to α ketophosphonates for enantioselective access to bioactive 2 pyranylphosphonates |
| topic | Science::Chemistry::Organic chemistry NHC Catalyst Enantioselectivities |
| url | https://hdl.handle.net/10356/138269 |
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