Catalyzed reformatsky reactions with ethyl bromofluoroacetate for the synthesis of α-fluoro-β-hydroxy acids
The presence of catalytic amounts of CeCl3 improves yields and simplifies procedure in the Reformatsky reactions of ethyl bromofluoroacetate with aldehydes and ketones to generate diastereomeric mixtures of α-fluoro-β-hydroxy esters, some of which can be separated by crystallization or column flash chromatography. Diastereomerically pure α-fluoro-β-hydroxy acids are obtained by mild alkaline hydrolysis of the resolved α-fluoro-β-hydroxy esters. Detailed NMR data of new α-fluoro-β-hydroxy esters and α-fluoro-β-hydroxy acids are also presented.
Ocampo,Dolbier, Jr.,Abboud,Zuluaga
p. 72 - 78
(2007/10/03)
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