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Paper | Regular issue | Vol 24, No. 2, 1986, pp.401-412
Published online, 1st January, 1970
DOI: 10.3987/R-1986-02-0401
Synthesis, Metalation and Electrophilic Quenching of Alkyl-isoxazole-4-tertiary Carboxamides. A Critical Comparison of Three Isoxazole Lateral Metalation Methods

Chorng-Shyr Niou and Nicholas R. Natale*

*Department of Chemistry, University of Idaho, 301 Renfrew Hall, Moscow, ID 83844-2343, U.S.A.


Alkyl-isoxazole-4-tertiary carboxamides are easily formed from isoxazole-4-carboxylic acids. Lateral metalation and electrophilic quenching was accomplished regioselectively at C-5 in synthetically useful yields. The chief advantage of this method is in the preparation of chiral isoxazole-4-tertiary carboxamides. The scope and limitations of this methodology is critically compared to lateral metalation of isoxazole-4-oxazolines and isoxazole carboxylic acid dianions.