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Synthesis 2000; 2000(6): 893-898
DOI: 10.1055/s-2000-6267
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Enantioselective Synthesis of α,α′-Disubstituted Piperidines via Ruthenium-Catalyzed Ring Rearrangement

Ulrike Voigtmann* , Siegfried Blechert
  • *Institut für Organische Chemie, Technische Universität Berlin, Straße des 17. Juni 135, D-10623 Berlin, Germany; Fax +49 (30) 31 42 36 19; E-mail: blechert@chem.tu-berlin.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A new method for the enantioselective synthesis of α,α′-disubstituted piperidines is described. Easily available cyclopentenones 5a,b rearrange via Ru-catalyzed RCM-ROM to heterocycles. Compound 6a is converted to the indolizidine 13.

metathesis - rearrangements - piperidines - indolizidines - azasugars - ruthenium - osmium - dihydroxylations