Asymmetric Synthesis of Cyclopropane-1,1-Dicarboxylates from a γ-Alkoxy-Alkylidenemalonate

Alain Krief; Laurent Provins; Alexandre Froidbise

doi:10.1055/s-1999-3173

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

Abstract

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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).

asymmetric synthesis - Michael adduct - cyclopropane derivative

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