Chiral organometallic reagents. Part XXIII.1 On the stereochemistry of the carbolithiation reaction of vinyl sulfides
Abstract
The intramolecular carbolithiation of vinyl sulfides at –105 °C in THF has been found to be stereospecific regarding the formation of the new carbon–carbon bond and non stereospecific regarding the formation of the new carbon–lithium bond. The resulting α-durylthioalkyllithium compounds are configurationally stable at –105 °C and epimerize at –90 °C.