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

Author(s): Michael North, Francesca Pizzato.

Journal Name: Letters in Organic Chemistry

Volume 6 , Issue 7 , 2009

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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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Article Details

VOLUME: 6
ISSUE: 7
Year: 2009
Page: [552 - 556]
Pages: 5
DOI: 10.2174/157017809789869465
Price: $65

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