Alkoxydienylstannanes via metalation of α,β-unsaturated and α-phenyl acetals: preparation and synthetic uses in the Stille cross-coupling reaction

摘要

Treatment of α,β-unsaturated (1 and 2) and α-phenyl (3) acetals with an equimolar mixture of butyllithium andnpotassium tert-butoxide (Schlosser’s reagent LIC–KOR) gives α-metalated 1,3-dienes and vinyl ethers that readilynreact with chlorotributyltin affording (Z)-functionalized alkoxyvinylstannanes 4–6. Stille cross-coupling reactionnbetween these reactants and allyl bromide, iodobenzene, or benzoyl chloride produces derivatives 7–13 that can benmoreover converted into carbonyl compounds 14–19 according to an umpolung approach.