A useful synthetic equivalent of a hydroxyacetone enolate

Abstract

Indium promoted allylation of carbonyl compounds with 4-(bromomethyl)-1,3- dioxol-2-one diastereoselectively affords anti-α,β-dihydroxyketones, protected as enol carbonates. These initial products can be deprotected to free dihydroxyketones or transformed under mild conditions into the corresponding cyclic carbonates, which constitutes a useful approach to hydroxyacetone aldols. © 2011 American Chemical Society.