Issue 41, 2015

Intramolecular thiol–yne cyclisation as a novel strategy for thioglycal synthesis

Abstract

A novel intramolecular thiol–yne cyclisation strategy has been developed for the synthesis of thioglycals. Both ionic and radical mediated cyclisation pathways have been investigated for D- and L-sugars. The ionic cyclisation provides exclusive access to 5-exo products directly from the thioesters whereas the radical cyclisation provides access to both 5-exo and 6-endo products upon photochemical irradiation of the free thiols. These are the first examples of intramolecular thiol–yne cyclisation reactions applied to thiosugar synthesis.

Graphical abstract: Intramolecular thiol–yne cyclisation as a novel strategy for thioglycal synthesis

Supplementary files

Article information

Article type
Communication
Submitted
13 Mar 2015
Accepted
20 Apr 2015
First published
20 Apr 2015

Chem. Commun., 2015,51, 8672-8674

Author version available

Intramolecular thiol–yne cyclisation as a novel strategy for thioglycal synthesis

V. Corcé, L. McSweeney, A. Malone and E. M. Scanlan, Chem. Commun., 2015, 51, 8672 DOI: 10.1039/C5CC02162F

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