Download PDF
Synlett 1996; 1996(11): 1117-1118
DOI: 10.1055/s-1996-5671
letter
© 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.

Novel Approach to Chiral Pyrrolidin-2-ylidene Carboxylates

Jacek G. Sosnicki1 , Jürgen Liebscher2
  • 1Department of Organic Chemistry, Technical University, 71-065 Szczecin, Al Piastów 42, Poland, Fax: 48(91)489486, e-mail sosnicki@carbon.chemn.tuniv.szczecin.pl
  • 2Institut für Chemie, Humboldt-Universität Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany, Fax: 49(30)2093 7343, e-mail liebscher@chemie.hu-berlin.de
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Michael addition of nitromethane to α,β-unsaturated thioamide 1 or α,β-unsaturated thiolactam 5 gives γ-nitrothioamides 2 or β-nitromethylthiolactams 6 and 7. Subsequent transformation to β-enaminoesters 3 and 8 by Eschenmoser reaction with ethyl bromoacetate and triethylphosphite followed by reduction of the nitro group and intramolecular addition of the resulting amino function to the β-position of the enaminoester moiety opens a novel access to chiral pyrrolidin-2-ylidene carboxylates 4 and 10, respectively.

pyrrolidin-2-ylidene carboxylate - ring transformation - Michael addition - thiolactams - nitromethane

      >