Palladium(0)-catalysed hydrostannylation of 1-alkoxy-1-alkynes: A synthesis of α-alkoxyalkenylstannanes and their transmetallation to α-alkoxyalkenyllithiums

Article abstract of DOI:10.1055/s-1993-26015

1-Alkoxy-1-alkynes undergo rapid hydrostannylation with trialkylstannanes in the presence of catalytic amounts of palladium(0). The reaction gives clean cis-addition with the tin being placed preferentially in the α-position. The resultant α-alkoxyalkenylstannanes transmetallate efficiently with BuLi to α-alkoxyalkenyllithiums which were previously accessible only with difficulty.