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Keywords:

  • Reduction;
  • Diastereoselectivity;
  • Nitrogen heterocycles;
  • (–)-Deoxocassine

Abstract

The chemo- and diastereoselective reduction of chiral piperidine β-enamino esters 4 and 6 and β-enamino ketones 5 and 7 was studied and found to afford 2,3- or 2,3,6-substituted piperidines. This approach was successfully applied to the total synthesis of (–)-deoxocassine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)