Convenient preparation of α-bromo-α-fluoro-β-hydroxyesters building blocks from aldehydes, ketones and lactones

A Reformatsky-type addition of ethyl dibromofluoroacetate associated with diethylzinc to various carbonyl compounds is described. Aldehydes, ketones and lactones were converted into the corresponding α-bromo-α-fluoro-β-hydroxyesters in good yields.

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Bibliographic Details
Published in:Tetrahedron letters 2011-05, Vol.52 (19), p.2473-2475
Main Authors: Zoute, Ludivine, Lemonnier, Gérald, Nguyen, Tanh Mai, Quirion, Jean-Charles, Jubault, Philippe
Format: Article
Language:English
Subjects:
Aldehydes
Aliphatic compounds
Carbonyl compounds
Chemistry
Diethylzinc
Ethyldibromofluoroacetate
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Ketones
Lactones
Organic chemistry
Preparations and properties
Reformatsky addition
Tetrahedrons
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Description
Summary:A Reformatsky-type addition of ethyl dibromofluoroacetate associated with diethylzinc to various carbonyl compounds is described. Aldehydes, ketones and lactones were converted into the corresponding α-bromo-α-fluoro-β-hydroxyesters in good yields.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2011.03.014