Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 21, Pages 6120-6124Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201800909
Keywords
2-deoxyglycosides; eosin Upsilon; photoacids; photocatalysis; visible light
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Funding
- University at Albany, State University of New York
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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 Upsilon. 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 alpha-selectivity.
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