期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 134, 期 28, 页码 11400-11403出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja305076b
关键词
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资金
- CNPq-Brazil
- Bristol-Myers Squibb
- NIHGMS [R01 01 GM07820-06]
A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
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