Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 48, Pages 17245-17248Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b09152
Keywords
-
Categories
Funding
- 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
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available