Revisiting the armed-disarmed concept: the importance of anomeric configuration in the activation of S-benzoxazolyl glycosides.
The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. rcrich@chem.wayne.edu
Li
Ming
M
D001555:Benzene Derivatives / Q000737:chemistry*; D003300:Copper / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry*; D013865:Thioglycosides / Q000138:chemical synthesis / Q000737:chemistry*
D001555:Benzene Derivatives; D006027:Glycosides; D010080:Oxazoles; D013865:Thioglycosides; D003300:Copper