Tetrahedron p. 6399 - 6412 (1990)
Update date:2022-08-02
Topics:
Verlhac, Jean-Baptiste
Pereyre, Michel
Quintard, Jean-Paul
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.
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