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Title: Enantioselective Reformatsky reaction of ethyl iododifluoroacetate with ketones.
Authors: Fornalczyk, M
Singh, K
Stuart, AM
First Published: 28-Apr-2012
Citation: ORG BIOMOL CHEM, 2012, 10 (16), pp. 3332-3342
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.
DOI Link: 10.1039/c2ob25081k
eISSN: 1477-0539
Type: Journal Article
Appears in Collections:Published Articles, Dept. of Chemistry

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