期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 141, 期 43, 页码 17062-17067出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b08510
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资金
- Ministry of Education of Singapore [R-143-000-A94-112]
- National University of Singapore [R-143-000-A57-114]
- Fundamental Research Funds for the Central Universities [05150-19GH020157]
We present herein an unprecedented stereoselective synthesis of bridged biaryls with defined axial and central chirality from readily available starting materials. This N-heterocyclic carbene-catalyzed method proceeds through propargylic substitution of azolium enolates followed by two-directional cyclization, as supported by DFT calculation. A range of benzofuran/indole-derived bridged biaryls bearing an eight-membered lactone are accessed with uniformly high stereoselectivity (>98:2 dr, mostly >98% ee).
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