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Title

A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids

AuthorsRos, Abel ; Álvarez, Eleuterio ; Dietrich, Hansjörg; Fernández, Rosario; Lassaletta, José M.
KeywordsAsymmetric synthesis
Cycloadditions
Heterocycles
Nitrile oxides
Isoxazolines
Issue Date27-Oct-2005
PublisherThieme
CitationSynlett (19): 2899-2904 (2005)
AbstractThe 1,3-dipolar cycloaddition of a variety of aromatic and aliphatic nitrile oxides to 2,5-trans-2,5-diphenylpyrrolidine ­derived acrylamide and cinnamamide efficiently affords the corresponding 4,5-dihydroisoxazole-5-carboxamides in a highly regio- and stereoselective manner. The cycloaddition of aliphatic nitrile oxides to the analogue methacrylamide proceeds also smoothly to afford the expected cycloadducts in moderate yields and very high regio- and stereoselectivity. In sharp contrast, aromatic nitrile ­oxides react with the same amide to afford 5-methyl-4,5-dihydroisoxazole-5-carboxamides in higher yields but as near 1:1 mixtures of diastereoisomers. Acid hydrolysis of these products afforded enantiopure 4,5-dihydroisoxazole-5-carboxylic acids.
Description6 páginas, 3 figuras, 1 tabla, 3 esquemas.
Publisher version (URL)http://dx.doi.org/10.1055/s-2005-921894
URIhttp://hdl.handle.net/10261/37861
DOI10.1055/s-2005-921894
ISSN0936-5214
Appears in Collections:(IIQ) Artículos
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