The tri-n-butyltin group as a novel stereocontrol element and synthetic handle in the aza-[2,3]-Wittig sigmatropic rearrangement

Article abstract of DOI:10.1016/S0040-4039(97)10477-4

The stereoselective trans hydrostannation of a non terminal alkynyl benzyl amine is described which furnished a tri-nbutyltin substituted aza- [2,3]-Wittig sigmatropic rearrangement precursor. Anionic rearrangement afforded a vinyl stannane product, in 71% yield with near complete control of diastereoselectivity. Subsequent transition metal catalysed carbon-carbon bond forming reactions gave potential precursors to novel unnatural amine acids in good to moderate yields.