Glycosylation catalyzed by a chiral Brønsted acid.
The use of a chiral Brønsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochemical outcome of the glycosylation processes, hinting that perhaps diastereocontrol of glycosylation processes may become achievable through the judicious use of chiral organic catalysts.
Cox
Daniel J
DJ
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.
Smith
Martin D
MD
Fairbanks
Antony J
AJ
D000143:Acids / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006031:Glycosylation; D013237:Stereoisomerism
D000143:Acids; D002241:Carbohydrates