Lewis Acid Catalyzed Diastereoselective Vinylogous Mannich Reaction Induced by O-Pivaloylated d-Galactosylamine as the Chiral Auxiliary: Stereoselective Synthesis of 6-Arylpiperidin-2-ones

Abstract

The diastereospecific formation of β-N-glycosidically linked α,β-unsaturated δ-aminocarbonyl derivatives, in the form of (S)-δ-amino-δ-arylpent-2-enoic ester, has been achieved in high yield via a vinylogous Mannich reaction, utilizing poly-O-pivaloylated d-galacosylamine as the chiral auxiliary. (S)-6-p-Tolylpiperidine-2-one can be stereoselectively synthesized from (S)-δ-amino-δ-arylpent-2-enoic ester by sequential hydrogenation of the double bond, cyclic lactam formation, and removal of the N-glycosidic auxiliary under basic conditions.

Key words

vinylogous Mannich reaction - carbohydrate - chiral auxiliary - stereoselective synthesis - 6-arylpiperidin-2-ones

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Crystallographic data for the structural analysis of compound 5b has been deposited at the Cambridge Crystallographic Data Centre under No. CCDC 802525. These data can be obtained free of charge by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: [phone]; E-mail: [e-mail].