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

Lookup NU author(s): Professor Michael North, Francesca Pizzato

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Abstract

N,N-Diaryl alpha-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.

Publication metadata

Author(s): North M, Pizzato F

Publication type: Article

Publication status: Published

Journal: Letters in Organic Chemistry

Year: 2009

Volume: 67

Issue: 7

Pages: 552-556

Date deposited: 01/07/2010

ISSN (print): 1570-1786

ISSN (electronic): 1875-6255

Publisher: Bentham Science Publishers Ltd.

URL: http://dx.doi.org/10.2174/157017809789869465

DOI: 10.2174/157017809789869465

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