Stereoselective synthesis of vicinal dilithioalkenes by addition of lithium metal, to carbon-carbon triple bonds

Article abstract of DOI:10.1016/S0040-4020(01)85287-X

The reaction of various cyclic and acyclic alkynes with lithium dust (2% sodium) to form vicinal dilithioalkenes has been investigated. Aliphatic alkynes, e.g. 3-hexyne (27a), exclusively afford the corresponding (E)-dilithioalkenes, insoluble solids which are stable at room temperature and allow access to a variety of tetrasubstituted olefins in acceptable yields.