Organocerium additions to hydrazones: effects of reagent

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J. Org. Chem. 1993,58, 569-578

Organocerium Additions to Hydrazones: Effects of Reagent Stoichiometry on Efficiency and Selectivity Scott E. Denmark: James P. Edwards, and Olivier Nicaise Roger A d a m s Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801 Received October 12, 1992

The effects of reagent stoichiometry on the efficiency and selectivity of organocerium additions to chiral and achiral hydrazones have been investigated. The reagent formed in-situ from 1equiv of CH3Li and 0.33 equiv of CeCl3 adds efficiently (>65% yield) to NJV-dimethylhydrazone1, but this same reagent reacts only sluggishly with chiral SAMEMP hydrazone 2 (