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

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

Document Type: Research Article

Publication date: 2009-10-01

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