A Facile One-pot Synthesis of Nα-Urethane Protected 3-Amino Alkyl Isoxazole-5-Carboxylic Acids and their Utility for the Preparation of Isoxazole-Linked Peptidomimetics
2011
Cu(I) catalyzed [3+2] cycloaddition of in situ generated Nα-Fmoc/Boc/Z-protected amino alkyl nitrile oxide with propiolic acid has led to a new class of 3,5-disubstituted isoxazole-bearing amino acid derivatives. The click chemistry protocol described herein is efficient in furnishing the isoxazole embedded amino acids. These unnatural synthons were subjected to chain extension on N- as well as C-termini to obtain 3,5-disubstituted isoxazole bearing di and tripeptidomimetics.
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