PDF herunterladen
Synthesis 1991; 1991(12): 1142-1146
DOI: 10.1055/s-1991-28406
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Diastereomeric 3,6-Diaminobicyclo[3.1.0]hexane Derivatives: A Stereocomplementary Approach

Elmar Vilsmaier* , Joachim Fath, Gerhard Maas
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Str., D-6750 Kaiserslautern, Germany
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
29. April 2002 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Diastereomeric (1α,3β,5α,6β)- and (1α,3α,5α,6β)-diaminobicyclo [3.1.0]hexane-6-carbonitriles 12 and 16 were synthesized with high stereoselectivity from 1,4-cyclohexanedione monoacetal 6 via chloroenamines 17 and 18, respectively. The sequence of reaction of 6 with a cyclic amine to give an enamine, chlorination with N-chlorosuccinimide and subsequent cyclopropanation with cyanide ion in the presence of a phase-transfer catalyst, cleavage of the acetal function followed by reductive amination, leads to 12. Changing the order of these synthetic steps allows an easy approach to 16. The configurations of 12 and 16 were established by 1H- and 13C-NMR data and an X-ray structural analysis of 16b.

      >