The preparation of optically active α-amino 4 H-[1,2,4]oxadiazol-5-ones from optically active α-amino acids

Optically active α-amino 4 H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipepti...

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Bibliographic Details
Published inTetrahedron Vol. 65; no. 46; pp. 9536 - 9541
Main Authors Mangette, John E., Johnson, Matthew R., Le, Van-Duc, Shenoy, Rajesh A., Roark, Howard, Stier, Michael, Belliotti, Thomas, Capiris, Thomas, Guzzo, Peter R.
Format Journal Article
LanguageEnglish
Published Elsevier Ltd 2009
Subjects
Bioisostere
Optically active
Oxadiazolone
α-Amino acid
Bioisostere
Oxadiazolone
Optically active
α-Amino acid
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Summary:Optically active α-amino 4 H-[1,2,4]oxadiazol-5-ones (oxadiazolones) were prepared from optically active α-amino acids in five synthetic steps. The oxadiazolone moiety serves as a bioisosteric replacement for the carboxylic acid. Incorporation of an α-amino oxadiazolone into a representative dipeptide mimic is described. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2009.09.045