A Preparation of <i>β</i>-Oxoester Enolate Equivalents from SmI2 and <i>α</i>-Bromoalkanoates

Abstract

Abstract A treatment of ethyl bromoacetate with two molar equivalent of samarium diiodide at −50 °C for 15 min in THF produces a β-oxoester enolate equivalent; the reagent reacts with ketones or aldehydes to give δ-hydroxy-β-oxoesters in excellent yields.