Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction?

Chemical Communications Pub Date: 2012-02-02 DOI: 10.1039/C2CC17985G

Abstract

The first enantioselective Reformatsky-type reaction of ethyl iodofluoroacetate has been accomplished with alkyl aryl ketones. High diastereoselectivities and excellent enantioselectivities for the major diastereomer (93–95% ee) were achieved with large alkyl groups. For smaller alkyl groups the diastereoselectivities were moderate, but excellent enantioselectivities were obtained for both diastereomers (79–94% ee).

Graphical abstract: Synthesis of α-fluoro-β-hydroxy esters by an enantioselective Reformatsky-type reaction
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