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.

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