Journal
NATURE CHEMISTRY
Volume 5, Issue 9, Pages 768-774Publisher
NATURE PUBLISHING GROUP
DOI: 10.1038/NCHEM.1708
Keywords
-
Categories
Funding
- US National Institutes of Health, Institute of General Medical Sciences [GM-57212]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM057212] Funding Source: NIH RePORTER
Ask authors/readers for more resources
Catalytic enantioselective monosilylations of diols and polyols furnish valuable alcohol-containing molecules in high enantiomeric purity. These transformations, however, require high catalyst loadings (20-30 mol%) and long reaction times (2-5 days). Here, we report that a counterintuitive strategy involving the use of an achiral co-catalyst structurally similar to the chiral catalyst provides an effective solution to this problem. A combination of seemingly competitive Lewis basic molecules can function in concert such that one serves as an achiral nucleophilic promoter and the other performs as a chiral Bronsted base. On the addition of 7.5-20 mol% of a commercially available N-heterocycle (5-ethylthiotetrazole), reactions typically proceed within one hour, and deliver the desired products in high yields and enantiomeric ratios. In some instances, there is no reaction in the absence of the achiral base, yet the presence of the achiral co-catalyst gives rise to facile formation of products in high enantiomeric purity.
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