Diastereoselective Additions to C,C Double Bonds Applied to the Enantioselective Synthesis of Pyrethroic Acids

Alain      Krief; Alexandre      Froidbise

doi:10.2174/157019305774322680

Abstract

Detailed review on enantioselective synthesis of methyl (1R)-trans-chrysanthemate and related methyl (1R)-cis-deltamethrinate is presented. These commercially available esters of vinylcyclopropanecarboxylic acids belong to pyrethroids class of insecticides. They are used as single enantiomers for domestic and agricultural purpose. They are almost 3.5 10 4 more active than DDT and are biodegradable.

Keywords: addition, vinyl cyclopropane carboxylic esters, cyclopropanation, sulfur ylides, phosphorus ylides, asymmetric induction, olefination reactions

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Mini-Reviews in Organic Chemistry

Title: Diastereoselective Additions to C,C Double Bonds Applied to the Enantioselective Synthesis of Pyrethroic Acids

Volume: 2 Issue: 4

Author(s): Alain Krief and Alexandre Froidbise

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Keywords: addition, vinyl cyclopropane carboxylic esters, cyclopropanation, sulfur ylides, phosphorus ylides, asymmetric induction, olefination reactions

Abstract: Detailed review on enantioselective synthesis of methyl (1R)-trans-chrysanthemate and related methyl (1R)-cis-deltamethrinate is presented. These commercially available esters of vinylcyclopropanecarboxylic acids belong to pyrethroids class of insecticides. They are used as single enantiomers for domestic and agricultural purpose. They are almost 3.5 10 4 more active than DDT and are biodegradable.

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Krief Alain and Froidbise Alexandre, Diastereoselective Additions to C,C Double Bonds Applied to the Enantioselective Synthesis of Pyrethroic Acids, Mini-Reviews in Organic Chemistry 2005; 2 (4) . https://dx.doi.org/10.2174/157019305774322680