Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors

Xu Dong; Li Chen; Zhitong Zheng; Xu Ma; Zaigang Luo; Liming Zhang

doi:10.1039/C8CC02494D

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Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors†

Xu Dong,^a Li Chen,

*^ab Zhitong Zheng,^b Xu Ma,^b Zaigang Luo^b and Liming Zhang

*^b

Author affiliations

* Corresponding authors

^a State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China
E-mail: chenliyss@nankai.edu.cn

^b Department of Chemistry and Biochemistry, University of California, Santa Barbara, CA 93106, USA
E-mail: zhang@chem.ucsb.edu

Abstract

A silver-catalyzed glycosylation reaction employing readily accessible and stable glycosyl ynenoates is developed. This reaction is mostly high yielding and exhibits varying levels of stereoinversion at the anomeric position. Compared to established and versatile Yu's gold catalysis, this chemistry features the use of substantially cheaper AgNTf₂.

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Article information

DOI: https://doi.org/10.1039/C8CC02494D
Article type: Communication
Submitted: 28 Mar 2018
Accepted: 21 Jun 2018
First published: 18 Jul 2018

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Chem. Commun., 2018,54, 8626-8629

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Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors

X. Dong, L. Chen, Z. Zheng, X. Ma, Z. Luo and L. Zhang, Chem. Commun., 2018, 54, 8626 DOI: 10.1039/C8CC02494D

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Chemical Communications

Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors†

Abstract

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Silver-catalyzed stereoselective formation of glycosides using glycosyl ynenoates as donors

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