Synlett 1989; 1989(1): 20-22
DOI: 10.1055/s-1989-34682
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Modified Proline Auxiliaries for Selective Addition of Organocerium Reagents to Hydrazones

Theodor Weber* , James P. Edwards, Scott E. Denmark
  • *Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA
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Publication History

Publication Date:
26 February 2002 (online)

A series of proline-derived hydrazines has been prepared and the reactions of their corresponding hydrazones with organocerium reagents have been examined. All of the hydrazones underwent smooth additions but the diastereoselectivity varied with the nature of the side chain. The (S)-1-amino-2-(2-methoxyethoxymethyl)pyrrolidine (SAMEMP) gave the highest selectivities overall for various nucleophiles.