期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 22, 页码 8169-8172出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja403535a
关键词
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资金
- National Basic Research Program of China (973 Program) [2009CB825300]
- National Natural Science Foundation of China [20923005, 21025209, 21121062]
Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features switching of the substituent from the indole C-3 position to the C-2 position (from the C-2 position to the C-3 position in the case of pyrrole) without loss of the enantiomeric purity, providing a novel concept in designing the asymmetric construction of enantiopure polycyclic indoles and pyrroles.
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