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Tosylhydrazones containing only tertiary a hydrogens react with lithium diisopropylamide (LDA) to yield trisubstituted alkenes. The reaction of these and other tosylhydrazones with LDA shows a high degree of regiospecificity which is controlled by the stereochemistry of the imino bond. The stereochemistry of the reaction is manifested by the dominance of the cis alkene except in cases where isomerization to the trans alkene has a low activation barrier. The reaction of LDA with tosylhydrazones of /3-keto esters is also successful.

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