Alkylated phenylthio hex-2-enopyranosides readily undergo 1,3-phenylthio migration, and treatment of the resulting enol ether with N-iodosuccinimide gives an allyl-oxocarbenium ion which can be trapped intramolecularly by a suitably located hydroxy group to yield an unsaturated spiroketal.
A. M. Gomez, S. Valverde and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1991, 1207 DOI: 10.1039/C39910001207
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