Synlett 1999; 1999(12): 1936-1938
DOI: 10.1055/s-1999-3173
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Asymmetric Synthesis of Cyclopropane-1,1-Dicarboxylates from a γ-Alkoxy-Alkylidenemalonate

Alain Krief* , Laurent Provins, Alexandre Froidbise
  • *Laboratoire de Chimie Organique de Synthèse, Département de Chimie, Facultés Universitaires Notre-Dame de la Paix, 61 rue de Bruxelles, B-5000 NAMUR, Belgium; Fax + 32 81 72 45 36; E-mail: alain.krief@fundp.ac.be
Further Information

Publication History

Publication Date:
31 December 1999 (online)

2-Metallo-2-sulfonylpropanes and 2-metallo-2-nitropropanes react with the dimethyl alkylidenemalonate derived from the acetonide of d-glyceraldehyde to produce the Michael adduct or the corresponding dimethyl cyclopropane-1,1-dicarboxylate. The nature of the product formed and the relative configuration of the cyclopropane derivative depends upon the nature of the leaving group and the conditions used (solvent and counter ion).