Journal
CHEMICAL SCIENCE
Volume 10, Issue 5, Pages 1426-1433Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8sc03587c
Keywords
-
Categories
Funding
- MEXT, Japan [23105002, JP17H06447]
Ask authors/readers for more resources
An F10BINOL-derived chiral phosphoric acid was shown to be an effective catalyst for an enantioselective carbonyl-ene reaction of 1,1-disubstituted olefins with ethyl glyoxylate as the common enophile. The perfluoro-binaphthyl skeleton is beneficial not only for adopting high catalytic activity but also for creating an effective chiral environment for enantioselective transformations. Indeed, the reaction afforded enantio-enriched homoallylic alcohols in high yields with high enantioselectivities. Theoretical studies identified that the multi-point C-H/O hydrogen bonds and the p interactions between the substrates and the 6-methoxy-2-naphthyl substituents at the 3,3 0 -positions of the F10BINOL skeleton play a crucial role in determining the stereochemical outcomes. The significance of the perfluorobinaphthyl skeleton in achieving the high enantioselectivity was also evaluated through a structural analysis of the catalysts.
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