期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 42, 页码 16961-16970出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b09303
关键词
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资金
- National Natural Science Foundation of China [21622204, 21772161, 91545105]
- Natural Science Foundation of Fujian Province of China [2019J02001]
- Xiamen University [20720180036]
- NFFTBS [J1310024]
- PCSIRT
- Science & Technology Cooperation Program of Xiamen [3502Z20183015]
The generation of metal carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. However, most of these transformations are based on the use of noble-metal catalysts and successful examples of such an asymmetric version are still very scarce. Here a copper-catalyzed enantioselective cascade cyclization of N-propargyl ynamides is reported, enabling the practical and atom-economical construction of diverse chiral polycyclic pyrroles in generally good to excellent yields with wide substrate scope and excellent enantioselectivities (up to 97:3 e.r.). Importantly, this protocol represents the first copper-catalyzed asymmetric diyne cyclization. Moreover, mechanistic studies revealed that the generation of donor/donor copper carbenes is presumably involved in this 1,5-diyne cyclization, which is distinctively different from the related gold catalysis, and thus it constitutes a novel way for the generation of donor/donor metal carbenes.
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