Premium
Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis
Author(s) -
Zhao Gaoyuan,
Wang Ting
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201800909
Subject(s) - chemistry , catalysis , selectivity , conjugated system , phenol , eosin y , stereoselectivity , organic chemistry , combinatorial chemistry , photochemistry , polymer , photocatalysis
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.