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|Title:||A Practical Synthesis of Enantiopure 4,5-Dihydroisoxazole-5-carboxylic Acids|
|Authors:||Ros, Abel; Álvarez, Eleuterio; Dietrich, Hansjörg; Fernández, Rosario; Lassaletta, José M.|
|Citation:||Synlett (19): 2899-2904 (2005)|
|Abstract:||The 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.|
|Description:||6 páginas, 3 figuras, 1 tabla, 3 esquemas.|
|Publisher version (URL):||http://dx.doi.org/10.1055/s-2005-921894|
|Appears in Collections:||(IIQ) Artículos|
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