Revisiting the Armed−Disarmed Concept: The Importance of Anomeric Configuration in the Activation of S-Benzoxazolyl Glycosides
- 22 September 2007
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (21), 4115-4118
- https://doi.org/10.1021/ol701466u
Abstract
The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-β-d-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive α-anomer, to be the result of neighboring group participation. Revision of the armed−disarmed concept for glycosyl donors is not required.Keywords
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