Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles
A carbene-catalyzed reaction between α-bromoenals and thioamides was developed. Key steps include enantioselective 1,4-addition of thioamide sulfur atoms to α,β-unsaturated acyl azolium intermediate. Subsequent intramolecular annulation eventually affords thiazinone heterocycles with high optical pu...
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sg-ntu-dr.10356-1377602023-02-28T19:46:30Z Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles Liu, Changyi Wu, Shuquan Xu, Jun Chen, Lingzhu Zheng, Pengcheng Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry::Organic chemistry Enantioselective Addition Carbene-catalyzed A carbene-catalyzed reaction between α-bromoenals and thioamides was developed. Key steps include enantioselective 1,4-addition of thioamide sulfur atoms to α,β-unsaturated acyl azolium intermediate. Subsequent intramolecular annulation eventually affords thiazinone heterocycles with high optical purities. The introduction of Lewis acid additives such as Cu(OTf)2 to this NHC catalytic reaction could provide small but consistent improvements to reaction enantioselectivities. NRF (Natl Research Foundation, S’pore) ASTAR (Agency for Sci., Tech. and Research, S’pore) MOE (Min. of Education, S’pore) Accepted version 2020-04-14T01:47:55Z 2020-04-14T01:47:55Z 2019 Journal Article Liu, C., Wu, S., Xu, J., Chen, L., Zheng, P., & Chi, R. Y. (2019). Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles. Organic Letters, 21(23), 9493-9496. doi:10.1021/acs.orglett.9b03685 1523-7060 https://hdl.handle.net/10356/137760 10.1021/acs.orglett.9b03685 31742417 2-s2.0-85075474932 23 21 9493 9496 en 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.9b03685 application/pdf |
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Science::Chemistry::Organic chemistry Enantioselective Addition Carbene-catalyzed Liu, Changyi Wu, Shuquan Xu, Jun Chen, Lingzhu Zheng, Pengcheng Chi, Robin Yonggui Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| description |
A carbene-catalyzed reaction between α-bromoenals and thioamides was developed. Key steps include enantioselective 1,4-addition of thioamide sulfur atoms to α,β-unsaturated acyl azolium intermediate. Subsequent intramolecular annulation eventually affords thiazinone heterocycles with high optical purities. The introduction of Lewis acid additives such as Cu(OTf)2 to this NHC catalytic reaction could provide small but consistent improvements to reaction enantioselectivities. |
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School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Liu, Changyi Wu, Shuquan Xu, Jun Chen, Lingzhu Zheng, Pengcheng Chi, Robin Yonggui |
| format |
Article |
| author |
Liu, Changyi Wu, Shuquan Xu, Jun Chen, Lingzhu Zheng, Pengcheng Chi, Robin Yonggui |
| author_sort |
Liu, Changyi |
| title |
Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| title_short |
Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| title_full |
Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| title_fullStr |
Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| title_full_unstemmed |
Carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| title_sort |
carbene-catalyzed enantioselective addition of thioamides to bromoenals for access to thiazinone heterocycles |
| publishDate |
2020 |
| url |
https://hdl.handle.net/10356/137760 |
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1759853517994983424 |