Journal of Organic Chemistry 2002-01-11

Catalyzed Reformatsky reactions with ethyl bromofluoroacetate for the synthesis of alpha-fluoro-beta-hydroxy acids.

R Ocampo, W R Dolbier, K A Abboud, F Zuluaga

Index: J. Org. Chem. 67(1) , 72-8, (2002)

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Abstract

The presence of catalytic amounts of CeCl(3) improves yields and simplifies procedure in the Reformatsky reactions of ethyl bromofluoroacetate with aldehydes and ketones to generate diastereomeric mixtures of alpha-fluoro-beta-hydroxy esters, some of which can be separated by crystallization or column flash chromatography. Diastereomerically pure alpha-fluoro-beta-hydroxy acids are obtained by mild alkaline hydrolysis of the resolved alpha-fluoro-beta-hydroxy esters. Detailed NMR data of new alpha-fluoro-beta-hydroxy esters and alpha-fluoro-beta-hydroxy acids are also presented.