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Synlett 1998; 1998(6): 652-654
DOI: 10.1055/s-1998-1725
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Novel and Stereocontrolled Synthesis of Enantiopure and Polyalkyl Substituted Piperidines

Christoph Schneider* , Christoph Börner
  • *Institut für Organische Chemie, Georg-August-Universität Göttingen, Tammannstr. 2, D-37077 Göttingen, Germany; Fax + 49(5 51)39 96 60; E-mail: cschnei1@gwdg.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A flexible and stereodivergent synthesis of enantiopure piperidines with up to four alkyl-substituted chiral centers is reported which proceeds by way of a double nucleophilic addition of primary amines to the 7-oxo-2-enimides 1. These in turn are accessible via the silyloxy-Cope rearrangement of chiral syn-aldol products.

piperidines - intramolecular conjugate addition - iminium ion - Cope rearrangement - aldol products