A Useful Horner Reagent for the Synthesis of Some α-Methyl-α,β-Unsaturated S-Propyl Thioesters

Ph. Coutrot; C. Charbonnier; C. Grison

doi:10.1055/s-1991-26369

Synthesis 1991; 1991(1): 23-26
DOI: 10.1055/s-1991-26369

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A Useful Horner Reagent for the Synthesis of Some α-Methyl-α,β-Unsaturated S-Propyl Thioesters

Ph. Coutrot^* , C. Charbonnier, C. Grison

^*Laboratoire de Chimie Organique II, URA CNRS 486, Campus Victor Grignard, Université de Nancy I, BP 239, F-54506 Vandoeuvreles-Nancy Cédex, France

Abstract

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S-Alkyl 2-(dialkoxyphosphoryl)alkanethioates 3 can readily be prepared by the reaction of 2-(dialkoxyphosphoryl)alkanoyl chlorides 1 with thiols 2 in the presence of triethylamine. Only S-propyl 2-(dialkoxyphosphoryl)propanethioate (3b) gave synthetically useful Horner reactions: it was converted into the α-potassiopropanethioate anion by treatment with potassium carbonate in a small amount of water at room temperature. The Horner reaction between this anion and aldehydes 4 gave various α,β-unsaturated thioesters 5 with an α-substituted methyl group. Application of this method to the cis/trans ethyl 2-formyl-3,3-dimethyl-1-cyclopropylcarboxylate esters 4f led to the 2-(propylthiocarbonyl)-2-propenyl pyrethroid derivatives 5f.

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