Abstract
Substituent effects on the alkylations of the dimethylhydrazones of 2,4- and 2,6-disubstituted cyclohexanones are reported. High axial selectivities are observed in the alkylations of cyano-substituted metalated hydrazones, but not with alkoxycarbonyl-substituted cases. Hydrazones of 2-substituted cyclohexanones appear to alkylate axially out of a conformer with the 2-substituent pseudoaxially disposed. The possible origins of the stereoselectivities are addressed in light of an X-ray crystal structure of lithiated cyclohexanone dimethylhydrazone.
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