Stereoselective Synthesis of 2-Deoxyglycosides from Glycals by Visible-Light-Induced Photoacid Catalysis

Gaoyuan Zhao; Ting Wang

doi:10.1002/anie.201800909

Stereoselective Synthesis of 2-Deoxyglycosides from Glycals by Visible-Light-Induced Photoacid Catalysis

Angew Chem Int Ed Engl. 2018 May 22;57(21):6120-6124. doi: 10.1002/anie.201800909. Epub 2018 Apr 27.

Authors

Gaoyuan Zhao¹, Ting Wang¹

Affiliation

¹ Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY, 12222, USA.

PMID: 29569307
DOI: 10.1002/anie.201800909

Abstract

The direct, photoacid-catalyzed synthesis of 2-deoxyglycosides from glycals is reported. A series of phenol-conjugated acridinium-based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford 2-deoxyglycosides in good yields and with excellent α-selectivity.

Keywords: 2-deoxyglycosides; eosin Y; photoacids; photocatalysis; visible light.

Publication types

Research Support, Non-U.S. Gov't