Diastereoselective Darzens Condensations of α-Haloamides: Influence of Aryl Substituents on Diastereoselectivity

Michael      North; Francesca      Pizzato

doi:10.2174/157017809789869465

Abstract

N,N-Diaryl α-haloamides undergo Darzens condensations with aldehydes induced by metal hydroxides. The diastereoselectivity of epoxide formation is strongly influenced by the electronic properties of the arylamide, which can be rationalised on the basis of the acidity of the substrate hydrogens and hence on reaction occurring under kinetic or thermodynamic control.

Keywords: Darzens condensation, metal hydroxide, aldehyde, proton-acidity, diastereoselectivity, epoxide

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Letters in Organic Chemistry

Title: Diastereoselective Darzens Condensations of α-Haloamides: Influence of Aryl Substituents on Diastereoselectivity

Volume: 6 Issue: 7

Author(s): Michael North and Francesca Pizzato

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Keywords: Darzens condensation, metal hydroxide, aldehyde, proton-acidity, diastereoselectivity, epoxide

Abstract: N,N-Diaryl α-haloamides undergo Darzens condensations with aldehydes induced by metal hydroxides. The diastereoselectivity of epoxide formation is strongly influenced by the electronic properties of the arylamide, which can be rationalised on the basis of the acidity of the substrate hydrogens and hence on reaction occurring under kinetic or thermodynamic control.

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North Michael and Pizzato Francesca, Diastereoselective Darzens Condensations of α-Haloamides: Influence of Aryl Substituents on Diastereoselectivity, Letters in Organic Chemistry 2009; 6 (7) . https://dx.doi.org/10.2174/157017809789869465