期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 48, 页码 17245-17248出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b09152
关键词
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资金
- Deutsche Forschungsgemeinschaft [ME 1805/13-1]
- U.S. National Science Foundation [NSF CHE1565669]
- CBBI Fellowship [NIH T32 GM075762]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [1565669] Funding Source: National Science Foundation
We report a visible -light -activated asymmetric beta-C(sp(3))-H functionalization of 2-acyl imidazoles and 2-acylpyridines with 1,2-dicarbonyl compounds (typically alpha-ketoesters) catalyzed by a tailored stereo genic -at-rhodium Lewis acid catalyst. The C-C bond formation products are obtained in high yields (up to 99%) and with excellent stereoselectivities (up to >20:1 dr and up to >99% ee). Experimental and computational studies support a mechanism in which a photoactivated Rh-enolate transfers a single electron to the 1,2-dicarbonyl compound followed by proton transfer and a subsequent stereocontrolled radical-radical recombination.
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