Stereoselective synthesis of beta-(chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: application to the synthesis of a masked triyne.

@article{Simpkins2003StereoselectiveSO,
  title={Stereoselective synthesis of beta-(chloro)vinylsilanes using a regio- and (E)-stereoselective bis-stannylation of unsymmetrically substituted butadiynes: application to the synthesis of a masked triyne.},
  author={Simon M. E. Simpkins and Benson M Kariuki and Caterina S. Arico and Liam R Cox},
  journal={Organic letters},
  year={2003},
  volume={5 21},
  pages={
          3971-4
        }
}
[reaction: see text] A highly regio- and stereoselective bis-stannylation of unsymmetrically substituted butadiyne 3 provides bis-stannane 4. Selective lithiation of the internal tin residue effects a 1,4-retro-Brook rearrangement to afford vinylsilane 5. This was elaborated into the novel diethynylethene 1, which also functions as a masked triyne.