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.
[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.
Simpkins
Simon M E
SM
School of Chemistry, University of Birmingham, Edgbaston, Birmingham B15 2TT, UK.
Kariuki
Benson M
BM
Aricó
Caterina S
CS
Cox
Liam R
LR