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Synlett 1993; 1993(8): 595-597
DOI: 10.1055/s-1993-22543
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Stereoselective Synthesis of Bicyclic Pyrrolidines and Piperidines via the Reductive Alkylation of Azides with Organyldichloroboranes - Intramolecular Nucleophilic Substitution Tandem Sequence

Jean-Michel Jego* , Bertrand Carboni, Abdullah Youssofi, Michel Vaultier
  • *Groupe de Recherche de Physicochimie Structurale, URA CNRS 704, Université de Rennes I, Avenue du Général Leclerc, F-35042 Rennes Cédex, France
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Publication Date:
19 March 2002 (online)

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ω-Halogenoalkyldichloroboranes are easily prepared in a stereocontrolled manner by hydroboration of ω-bromoalkylcycloalkenes or Diels-Alder reaction of (E)-alkenyldichloroboranes. Amination with benzylazide followed by an intramolecular nucleophilic substitution afforded the corresponding trans-pyrrolidines or piperidines