"Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2--Se" by Dancan K. Njeri, Erik Alvarez Valenzuela et al.

Faculty Publications

Title

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

Authors

Dancan K. Njeri, Department of Chemistry, Louisiana State University 232 Choppin Hall, Baton Rouge, Louisiana 70806, United States.
Erik Alvarez Valenzuela, Department of Chemistry, Louisiana State University 232 Choppin Hall, Baton Rouge, Louisiana 70806, United States.
Justin R. Ragains, Department of Chemistry, Louisiana State University 232 Choppin Hall, Baton Rouge, Louisiana 70806, United States.

Document Type

Article

Publication Date

11-5-2021

Abstract

Here, we demonstrate that substitution of the benzyl groups of glucosyl imidate donors with trifluoromethyl results in a substantial increase in 1,2--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--trifluoromethylbenzyl). Particularly encouraging is that we observe high 1,2--selectivity with reactive alcohol acceptors.

Publication Source (Journal or Book title)

Organic letters

First Page

8214

Last Page

8218

Recommended Citation

Njeri, D. K., Valenzuela, E. A., & Ragains, J. R. (2021). Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2--Selective Glucosylation of Reactive Alcohols. Organic letters, 23 (21), 8214-8218. https://doi.org/10.1021/acs.orglett.1c02947

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