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Synlett 2004(15): 2791-2793  
DOI: 10.1055/s-2004-835639
LETTER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Chiral α-Amino-diazoketones on Solid Support: An Access to β-Homologated Amino Acid Derivatives

Sonia Cantel, Jean Martinez, Jean-Alain Fehrentz*
Laboratoire des Aminoacides, Peptides et Protéines (LAPP), UMR 5810 CNRS Universités Montpellier I et II, Faculté de Pharmacie, 15 Avenue Charles Flahault, BP 14491, 34093 Montpellier Cédex 5, France
Fax: +33(4)67548651; e-Mail: fehrentz@colombes.pharma.univ-montp1.fr;
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Publication History

Received 31 August 2004
Publication Date:
08 November 2004 (online)

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Abstract

Diazoketone derivatives were obtained on solid support from their corresponding α-amino acids anchored by their N-terminus to the resin. A complete study was performed to optimize the two steps process of this synthesis on solid support: activation of the carboxylic acid function followed by reaction with diazomethane. The obtained diazoketones were then submitted to Wolff rearrangement in the presence of an amine to yield the corresponding ­homologated amides or in the presence of water to yield the corresponding β-homologated amino acids.

Key words

α-amino-diazoketone - Wolff rearrangement - solid-phase synthesis - inverse anchoring