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

Dancan K NjeriErik Alvarez ValenzuelaJustin R Ragains
Published in: Organic letters (2021)
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.
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