Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 25, Pages 7939-7945Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b03444
Keywords
-
Categories
Funding
- Pfizer
- Boehringer-Ingelheim
- National Institute of General Medical Science of the National Institutes of Health [GM-068649]
Ask authors/readers for more resources
We report the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates. Our mechanistic studies suggest that distal stereocontrol is achieved through a Cs-bridged interaction between the Lewis basic C-terminal carboxylate of the peptides with the distal arene of the substrate.
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