期刊
ORGANIC LETTERS
卷 21, 期 13, 页码 5026-5029出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b01624
关键词
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资金
- National Natural Science Foundation of China [21772029, 21472028, 21807019]
- Natural Science Foundation of Guizhou University [GZU[2017]35]
- Opening Foundation of the Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University [2018GDGP0101]
- Guizhou University
- Guizhou Province First-Class Disciplines Project [GNYL(2017)008]
- Guizhou University of Traditional Chinese Medicine
- Singapore National Research Foundation [NRF-NRFI2016-06]
- Ministry of Education of Singapore [MOE2013-T2-2-003, MOE2016-T2-1-032, RG108/16]
- A*STAR Individual Research Grant [A1783c0008]
- Nanyang Technological University
- Nanyang Research Award Grant
The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp(2) carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.
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