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

[Image: see text] 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 o...

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Autores principales: Njeri, Dancan K., Valenzuela, Erik Alvarez, Ragains, Justin R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576833/
https://www.ncbi.nlm.nih.gov/pubmed/34677075
http://dx.doi.org/10.1021/acs.orglett.1c02947
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author Njeri, Dancan K.
Valenzuela, Erik Alvarez
Ragains, Justin R.
author_facet Njeri, Dancan K.
Valenzuela, Erik Alvarez
Ragains, Justin R.
author_sort Njeri, Dancan K.
collection PubMed
description [Image: see text] 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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spelling pubmed-85768332021-11-10 Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols Njeri, Dancan K. Valenzuela, Erik Alvarez Ragains, Justin R. Org Lett [Image: see text] 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. American Chemical Society 2021-10-22 2021-11-05 /pmc/articles/PMC8576833/ /pubmed/34677075 http://dx.doi.org/10.1021/acs.orglett.1c02947 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Njeri, Dancan K.
Valenzuela, Erik Alvarez
Ragains, Justin R.
Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title_full Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title_fullStr Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title_full_unstemmed Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title_short Leveraging Trifluoromethylated Benzyl Groups toward the Highly 1,2-Cis-Selective Glucosylation of Reactive Alcohols
title_sort leveraging trifluoromethylated benzyl groups toward the highly 1,2-cis-selective glucosylation of reactive alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8576833/
https://www.ncbi.nlm.nih.gov/pubmed/34677075
http://dx.doi.org/10.1021/acs.orglett.1c02947
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