Enantioselective Reformatsky reaction of ethyl iododifluoroacetate with ketones?

Organic & Biomolecular Chemistry Pub Date: 2012-02-23 DOI: 10.1039/C2OB25081K

Abstract

Two approaches have been developed for the enantioselective Reformatsky reaction of ethyl iododifluoroacetate with ketones to form a quaternary carbon centre using (1R,2S)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol as the chiral ligand. Good yields and high enantioselectivities (80–91% ee) were achieved with a range of alkyl aryl ketones in a convenient one-pot protocol using ethyl iododifluoroacetate and diethylzinc to form the difluorinated Reformatsky reagent homogeneously. In the traditional two-step Reformatsky reaction using the preformed Reformatsky reagent generated from ethyl iododifluoroacetate and zinc dust, good yields and good enantioselectivities (75–84% ee) were also obtained.

Graphical abstract: Enantioselective Reformatsky reaction of ethyl iododifluoroacetate with ketones
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