Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates
A carbene-catalyzed enantioselective addition of enals to five-membered cyclic imines is developed. The reaction gives chiral quaternary α-amino phosphonates bearing tetrasubstituted carbon centers with excellent enantioselectivities. The imine substrates can be generated in situ from the correspond...
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sg-ntu-dr.10356-1382892023-02-28T19:26:53Z Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates Sun, Jun Mou, Chengli Wang, Zhongyao He, Fangcheng Wu, Jian Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Carbene-catalyzed Enantioselective A carbene-catalyzed enantioselective addition of enals to five-membered cyclic imines is developed. The reaction gives chiral quaternary α-amino phosphonates bearing tetrasubstituted carbon centers with excellent enantioselectivities. The imine substrates can be generated in situ from the corresponding amines under an oxidative condition that is compatible with the carbene catalysis. Thus, a one-pot cross-dehydrogenative-coupling (CDC) reaction between enals and amines is also realized with high enantioselectivity remaining. The method provides quick enantioselective access to amino phosphonates with potential applications in medicines and pesticides. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-30T04:21:54Z 2020-04-30T04:21:54Z 2018 Journal Article Sun, J., Mou, C., Wang, Z., He, F., Wu, J., & Chi, R. Y. (2018). Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates. Organic letters, 20(18), 5969-5972. doi:10.1021/acs.orglett.8b02707 1523-7060 https://hdl.handle.net/10356/138289 10.1021/acs.orglett.8b02707 30211562 2-s2.0-85053661842 18 20 5969 5972 en Organic letters © 2018 American Chemical Society. All rights reserved. This paper was published in Organic letters and is made available with permission of American Chemical Society. application/pdf |
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Science::Chemistry::Organic chemistry Carbene-catalyzed Enantioselective Sun, Jun Mou, Chengli Wang, Zhongyao He, Fangcheng Wu, Jian Chi, Robin Yonggui Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| description |
A carbene-catalyzed enantioselective addition of enals to five-membered cyclic imines is developed. The reaction gives chiral quaternary α-amino phosphonates bearing tetrasubstituted carbon centers with excellent enantioselectivities. The imine substrates can be generated in situ from the corresponding amines under an oxidative condition that is compatible with the carbene catalysis. Thus, a one-pot cross-dehydrogenative-coupling (CDC) reaction between enals and amines is also realized with high enantioselectivity remaining. The method provides quick enantioselective access to amino phosphonates with potential applications in medicines and pesticides. |
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School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Sun, Jun Mou, Chengli Wang, Zhongyao He, Fangcheng Wu, Jian Chi, Robin Yonggui |
| format |
Article |
| author |
Sun, Jun Mou, Chengli Wang, Zhongyao He, Fangcheng Wu, Jian Chi, Robin Yonggui |
| author_sort |
Sun, Jun |
| title |
Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| title_short |
Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| title_full |
Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| title_fullStr |
Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| title_full_unstemmed |
Carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| title_sort |
carbene-catalyzed [4 + 2] cycloadditions of vinyl enolate and (in situ generated) imines for enantioselective synthesis of quaternary α-amino phosphonates |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/138289 |
| _version_ |
1759854147546382336 |