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Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives

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Stereoselective Synthesis of 3-Substituted and 3,4-Disubstituted Piperidine und Piperidin-2-one Derivatives

Ellen Klegraf and Horst Kunz

Institut f¨ur Organische Chemie, Universit¨at Mainz, Duesbergweg 10–14, 55128 Mainz, Germany Reprint requests to Prof. Dr. Horst Kunz. Fax: +49 6131 39 24786. Email: hokunz@uni-mainz.de Z. Naturforsch.2012,67b,389 – 405; received February 13, 2012

The stereoselective synthesis of 3-substituted and 3,4-disubstituted piperidine and piperidin-2-one derivatives was achieved starting from 2-pyridone. After N-galactosylation and subsequentO-sil- ylation, nucleophilic addition of organometallic reagents proceeded with high regio- and stereo- selectivity at 4-position. Substituents at position 3 were stereoselectively introduced by reaction of electrophiles with amide enolates of theN-galactosyl-2-piperidones.

Key words: N-Galactosyl Pyridone, 3-Alkyl-piperidines, 3,4-Dialkyl-piperidines, Carbohydrate Auxiliaries, Stereoselective Reactions

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