Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters

Anders Palmelund, Robert Madsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A procedure is described for acyloxyallylation of unprotected aldoses with two functionalized reagents: 3-bromopropenyl acetate and 3-bromopropenyl benzoate. The reaction is performed in ethanol or a dioxane/water mixture in the presence of indium metal. The products are deesterified in the workup to afford unsaturated polyols, which are isolated as mixtures of two diastereomers. The major diastereomers are subjected to ozonolysis to afford new aldoses, which have been elongated by two carbon atoms compared to the starting materials. The new aldoses all have lyxo configuration at positions 2, 3, and 4.
Original languageEnglish
JournalThe Journal of Organic Chemistry
Volume70
Issue number20
Pages (from-to)8248-8251
ISSN0022-3263
DOIs
Publication statusPublished - 2005

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