4.8 Article

Revisiting the armed-disarmed concept: The importance of anomeric configuration in the activation of S-Benzoxazolyl glycosides

Journal

ORGANIC LETTERS
Volume 9, Issue 21, Pages 4115-4118

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol701466u

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Funding

  1. NIGMS NIH HHS [R01 GM062160, GM62160, R01 GM062160-07] Funding Source: Medline

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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.

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