A useful synthetic equivalent of an acetone enolate

Abstract

2-Methoxymethoxy-3-chloropropene derived organometallics act as synthetic equivalents of an acetone enolate. Indium-promoted reaction of this reagent with aldehydes affords aldol adducts in moderate to excellent yields. When the reaction was performed with zinc, aldol products were isolated in protected form as the corresponding MOM-enol ethers.