Axial chirality in 1,4-disbustituted (ZZ)-1,3-dienes. Surprisingly low energies of activation for the enantiomerization in synthetically useful fluxional molecules

Trialkylsilyltrialkylstannes (R3Si-SnR'3) add to 1,6-diynes in the presence of Pd(0) and trispentaflurophenylphosphine to give 1,2-dialkylidenecyclopentanes with terminal silicon and tin substituents. The (ZZ)-geometry of these s-cis-1,3-dienes, resulting from the organometallic reaction mechanism involved, forces the silicon and tin groups to be nonplanar, thus making the molecules axially chiral.