A Useful Synthetic Equivalent of a Hydroxyacetone Enolate

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.

铟促进的羰基化合物与4-(溴甲基)-1,3-二氧戊环-2-酮(4-(bromomethyl)-1,3-dioxol-2-one)的烯丙基化反应，可非对映选择性地得到以烯醇碳酸酯形式保护的反式α,β-二羟基酮。该初始产物既可经脱保护得到游离的二羟基酮，也可在温和条件下转化为相应的环状碳酸酯，这为羟基丙酮类羟醛产物的合成提供了一种实用路径。