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Synlett 1996; 1996(11): 1117-1118
DOI: 10.1055/s-1996-5671
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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
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Publication Date:
31 December 2000 (online)

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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