Organotin homoenolate equivalents - access to β-acyl-and β-aryl-propionaldehydes through heterosubstituted allyltins and vinyltins

Abstract

Although, α-ethoxycrotyltributyltin can be used as an equivalent of the homoenolate anion CH 3 -CHCH 2CHO in reaction with acyl chlorides, the non-substituted α-ethoxyallyltributyltin could not be employed in this way. γ-Methoxyvinyltins, easily prepared by hydrostannation of propargylic ethers, are successfully employed as synthetic equivalents of the homoenolate anions -CH 2CH 2CHO and -CH 2CH 2COCH 3 in reactions with acyl chlorides. A silylated γ-methoxyvinyltin, which is both a vinyltin and an allylsilane, reacts with acyl chlorides and aryl bromides as a promising equivalent of the homoenolate anion -CH 2CH 2CHO and tolerates a wide range of other reactive functional groups.