Highly Efficient Hydroxylation of Carbonyl Compounds with Dimethyldioxirane

Abstract

Abstract The enolates and/or enols of ketones, esters, β‐diketones, β‐oxo esters, and β‐oxo lactones were transformed by dimethyl‐dioxirane (isolated in acetone solution or generated in situ) into their α‐hydroxy compounds in good to excellent yields. The direct hydroxylation of the enols was significantly enhanced by the use of fluoride ion. For the enolate of camphor the exo/endo diastereoselectivity depended significantly on the metal ligand; the highest exo/endo ratio (93:7) was observed for the enol trimethylsilyl ether of camphor.