Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis
A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted...
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sg-ntu-dr.10356-1550782023-02-28T19:57:18Z Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis Nie, Guihua Huang, Xuan Wang, Zhongyao Pan,Dingwu Zhang, Junmin Chi, Robin Yonggui School of Physical and Mathematical Sciences Science::Chemistry Aldehydes Catalysis A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities. Agency for Science, Technology and Research (A*STAR) Economic Development Board (EDB) Ministry of Education (MOE) Nanyang Technological University National Research Foundation (NRF) Accepted version We acknowledge financial support from the National Natural Science Foundation of China (21772029, 21801051, 21961006, 82360589, and 81360589), The 10 Talent Plan (Shicengci) of Guizhou Province ([2016]5649), the Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2], the Science and Technology Department of Guizhou Province ([2018]2802, [2019]1020), the Program of Introducing Talents of Discipline to Universities of China (111 Program, D20023) at Guizhou University, Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004], the Guizhou Province First-Class Disciplines Project [(Yiliu Xueke Jianshe Xiangmu)-GNYL(2017)008], Guizhou University of Traditional Chinese Medicine (China), and Guizhou University. Singapore National Research Foundation under its NRF Investigatorship (NRF-NRFI2016-06) and Competitive Research Program (NRF-CRP22-2019-0002); the Ministry of Education, Singapore, under its MOE AcRF Tier 1 Award (RG108/16, RG5/19, RG1/18), MOE AcRF Tier 2 (MOE2019-T2-2-117), MOE AcRF Tier 3 Award (MOE2018-T3-1- 003), the Agency for Science, Technology and Research (A*STAR) under its A*STAR AME IRG Award (A1783c0008, A1783c0010), GSK-EDB Trust Fund, and Nanyang Research Award Grant, Nanyang Technological University are acknowledged. 2022-02-10T06:32:03Z 2022-02-10T06:32:03Z 2021 Journal Article Nie, G., Huang, X., Wang, Z., Pan, D., Zhang, J. & Chi, R. Y. (2021). Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis. Organic Chemistry Frontiers, 8(18), 5105-5111. https://dx.doi.org/10.1039/d1qo00826a 2052-4129 https://hdl.handle.net/10356/155078 10.1039/d1qo00826a 2-s2.0-85115190272 18 8 5105 5111 en NRF-NRFI2016-06 NRF-CRP22-2019-0002 RG108/16 RG5/19 RG1/18 MOE2019-T2-2-117 MOE2018-T3-1- 003 A1783c0008 A1783c0010 Organic Chemistry Frontiers © 2021 The Partner Organisations. All rights reserved. This paper was published by Royal Society of Chemistry in Organic Chemistry Frontiers and is made available with permission of The Partner Organisations. application/pdf |
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Science::Chemistry Aldehydes Catalysis Nie, Guihua Huang, Xuan Wang, Zhongyao Pan,Dingwu Zhang, Junmin Chi, Robin Yonggui Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| description |
A carbene-catalyzed formal umpolung of donor-acceptor (D-A) cyclopropanes is disclosed. The cyclopropane moiety is connected to an acetyl aldehyde that can be activated by a carbene catalyst. The initially electrophilic carbon attached to the donor group of the D-A cyclopropane aldehyde is inverted to form a nucleophilic reaction center. A subsequent reaction with isatins via a formal [3 + 2] process forms lactones bearing multiple functional groups with excellent enantio- and diastereoselectivities. |
| author2 |
School of Physical and Mathematical Sciences |
| author_facet |
School of Physical and Mathematical Sciences Nie, Guihua Huang, Xuan Wang, Zhongyao Pan,Dingwu Zhang, Junmin Chi, Robin Yonggui |
| format |
Article |
| author |
Nie, Guihua Huang, Xuan Wang, Zhongyao Pan,Dingwu Zhang, Junmin Chi, Robin Yonggui |
| author_sort |
Nie, Guihua |
| title |
Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| title_short |
Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| title_full |
Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| title_fullStr |
Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| title_full_unstemmed |
Umpolung of donor-acceptor cyclopropanes : via N-heterocyclic carbene organic catalysis |
| title_sort |
umpolung of donor-acceptor cyclopropanes : via n-heterocyclic carbene organic catalysis |
| publishDate |
2022 |
| url |
https://hdl.handle.net/10356/155078 |
| _version_ |
1759857162559946752 |