A Preparation of β-Oxoester Enolate Equivalents from SmI2 and α-Bromoalkanoates

Article abstract of DOI:10.1246/cl.1995.197

A treatment of ethyl bromoacetate with two molar equivalent of samarium diiodide at -50 deg 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.