ORGANOTIN HOMOENOLATE EQUIVALENTS - ACCESS TO β-ACYL- AND β-ARYL-PROPIONALDEHYDES THROUGH HETEROSUBSTITUTED ALLYLTINS AND VINYLTINS

Article abstract of DOI:10.1016/S0040-4020(01)96010-7

Although, α-ethoxycrotyltributyltin can be used as an equivalent of the homoenolate anion CH3^-CHCH2CHO in reactions 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 ^-CH2CH2CHO and ^-CH2CH2COCH3 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 ^-CH2CH2CHO and tolerates a wide range of other reactive functional groups.