NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives
An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-be...
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sg-ntu-dr.10356-1702812023-09-06T00:55:16Z NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives Ji, Hong Zou, Juan Mou, Chengli Liu, Yonggui Ren, Shi-Chao Chi, Robin Yonggui School of Chemistry, Chemical Engineering and Biotechnology Engineering::Bioengineering Aldehyde Bismerthiazol An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC). Ministry of Education (MOE) National Research Foundation (NRF) We acknowledge funding support from the National Natural Science Foundation of China (22061007, 22071036), Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY number (2020)004], The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020), Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06) and Competitive Research Program (NRF-CRP22-2019-0002), and Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG7/20, RG5/19), MOE AcRF Tier 2 (MOE2019-T2-2-117), and MOE AcRF Tier 3 Award (MOE2018-T3-1-003). 2023-09-06T00:55:16Z 2023-09-06T00:55:16Z 2023 Journal Article Ji, H., Zou, J., Mou, C., Liu, Y., Ren, S. & Chi, R. Y. (2023). NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives. Chemical Communications, 59(42), 6351-6354. https://dx.doi.org/10.1039/d3cc00999h 1359-7345 https://hdl.handle.net/10356/170281 10.1039/d3cc00999h 37158205 2-s2.0-85159166457 42 59 6351 6354 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG7/20 RG5/19 MOE2019-T2-2-117 MOE2018-T3-1-003 Chemical Communications © 2023 The Royal Society of Chemistry. All rights reserved. |
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Engineering::Bioengineering Aldehyde Bismerthiazol Ji, Hong Zou, Juan Mou, Chengli Liu, Yonggui Ren, Shi-Chao Chi, Robin Yonggui NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| description |
An N-heterocyclic carbene (NHC) catalyzed enantio- and diastereoselective [12+2] cycloaddition is disclosed to rapidly construct sophisticated molecules bearing a tricyclic core and morpholine moiety. The success of our reaction relies on the NHC-catalyzed remote sp3 (C-H) bond activation of a 5H-benzo[a]pyrrolizine-3-carbaldehyde under oxidative conditions. Preliminary studies revealed that our products exhibit superior in vitro bioactivities against two plant pathogens to commercial Bismerthiazol (BT) and Thiodiazole Copper (TC). |
| author2 |
School of Chemistry, Chemical Engineering and Biotechnology |
| author_facet |
School of Chemistry, Chemical Engineering and Biotechnology Ji, Hong Zou, Juan Mou, Chengli Liu, Yonggui Ren, Shi-Chao Chi, Robin Yonggui |
| format |
Article |
| author |
Ji, Hong Zou, Juan Mou, Chengli Liu, Yonggui Ren, Shi-Chao Chi, Robin Yonggui |
| author_sort |
Ji, Hong |
| title |
NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| title_short |
NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| title_full |
NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| title_fullStr |
NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| title_full_unstemmed |
NHC-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| title_sort |
nhc-catalyzed [12+2] reaction of polycyclic arylaldehydes for access to indole derivatives |
| publishDate |
2023 |
| url |
https://hdl.handle.net/10356/170281 |
| _version_ |
1779156666394083328 |