jo051297s_si_001.pdf (97.67 kB)
Chain Elongation of Aldoses by Indium-Mediated Coupling with 3-Bromopropenyl Esters
journal contribution
posted on 2005-09-30, 00:00 authored by Anders Palmelund, Robert MadsenA 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.