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Synlett 1992; 1992(1): 89-93
DOI: 10.1055/s-1992-21278
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Enantioselective Synthesis of 3,3-Disubstituted 4-Piperidinones on Neutral Alumina

Elena L. Gaidarova* , Galina V. Grishina
  • *Department of Chemistry, Moscow State University, Moscow 119899, USSR
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Publication Date:
18 September 2002 (online)

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The asymmetric synthesis of 3,3-disubstituted 4-piperidinones has been performed on neutral alumina without a solvent by Michael-type alkylation of chiral imine derivatives of 3-substituted 4-piperidinones with electron-deficient alkenes. The highest enantioselectivity has been achieved using (S)- or (R)-1-phenylethylamine as a chiral auxiliary. The enantioselectivity of the alkylation depends on the structure of the 4-piperidinones and the chiral amines. The enantiomeric excess of the new (+)- and (-)-enantiomers of 3,3-disubstituted 4-piperidinones was established by 1 H NMR spectroscopy using chiral shift reagents and their absolute configuration was determined by circular dichroism curve correlation.