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Synthesis 1990; 1990(10): 871-874
DOI: 10.1055/s-1990-27037
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Diastereoselective Dealkoxycarbonylation of Sulfur-Substituted Dialkyl Cyclopropane-1,1-dicarboxylates

Angela M. Bernard* , Giovanni Cerioni, P. Paolo Piras, Gianfranco Seu
  • *Istituto di Chimica Farmaceutica, Tossicologica ed Applicata, Via Ospedale 72, 09100 Cagliari, Italy
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Publication Date:
17 September 2002 (online)

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In the dealkoxycarbonylation of dimethyl 2,2-dimethylcyclo- propane-1,1-dicarboxylate, 3-alkylthio or 3-arylthio substituents induce moderate diastereoselection. The analogous dealkoxycarbonylation of 3-alkylsulfonyl- or 3-arylsulfonyl-substituted cyclopropanes leads to an E diastereoselectivity of 100%.