A route to unsaturated spiroketals from phenylthio hex-2-enopyranosides via sequential alkylation, allylic rearrangement and intramolecular glycosidation
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 17,p. 1207-1208
- https://doi.org/10.1039/c39910001207
Abstract
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.Keywords
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