Journal
ORGANIC CHEMISTRY FRONTIERS
Volume 8, Issue 18, Pages 5105-5111Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1qo00826a
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Funding
- National Natural Science Foundation of China [21772029, 21801051, 21961006, 82360589, 81360589D]
- 10 Talent Plan (Shicengci) of Guizhou Province [[2016]5649]
- Guizhou Province Returned Oversea Student Science and Technology Activity Program [(2014)-2]
- Science and Technology Department of Guizhou Province [[2018]2802, [2019]1020]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) at Guizhou University [D20023]
- Frontiers Science Center for Asymmetric Synthesis and Medicinal Molecules, Department of Education, Guizhou Province [Qianjiaohe KY (2020)004]
- Guizhou Province First-Class Disciplines Project [GNYL(2017)008]
- Guizhou University of Traditional Chinese Medicine (China)
- Guizhou University
- Singapore National Research Foundation [NRF-NRFI2016-06, NRF-CRP22-2019-0002]
- Ministry of Education, Singapore [RG108/16, RG5/19, RG1/18, MOE2019-T2-2-117, MOE2018-T3-1-003]
- Agency for Science, Technology and Research (A*STAR) [A1783c0008, A1783c0010]
- GSK-EDB Trust Fund
- Nanyang Technological University
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A carbene-catalyzed formal umpolung reaction of donor-acceptor cyclopropanes has been revealed, where the electrophilic carbon attached to the donor group of the cyclopropane aldehyde is inverted to a nucleophilic reaction center. Subsequent reaction with isatins via a formal [3 + 2] process forms lactones with multiple functional groups and excellent enantio- and diastereoselectivities.
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.
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