Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols.

ABSTRACT: 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.

SUBMITTER: Njeri DK 

PROVIDER: S-EPMC8576833 | biostudies-literature | 2021 Nov

REPOSITORIES: biostudies-literature