Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8214-8218Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02947
Keywords
-
Categories
Funding
- National Science Foundation [CHE1665208, CHE-2101153]
Ask authors/readers for more resources
By substituting the benzyl groups of glucosyl imidate donors with trifluoromethyl, a substantial increase in 1,2-cis-selectivity can be achieved when activated with TMS-I in the presence of triphenylphosphine oxide. The stereoselectivity depends on the number of trifluoromethyl groups, leading to high 1,2-cis-selectivity with reactive alcohol acceptors.
Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2-cis-selectivity when activated with TMS-I in the presence of triphenylphosphine oxide. Stereoselectivity is dependent on the number of trifluoromethyl groups (4-trifluoromethylbenzyl vs 3,5-bis-trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2-cis-selectivity with reactive alcohol acceptors.
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