Cross-Claisen Condensation of N -Fmoc-Amino Acids - A Short Route to Heterocyclic γ-Amino Acids - Université de Montpellier
Article Dans Une Revue European Journal of Organic Chemistry Année : 2015

Cross-Claisen Condensation of N -Fmoc-Amino Acids - A Short Route to Heterocyclic γ-Amino Acids

Résumé

4-Amino(methyl)-1,3-thiazole-5-carboxylic acids (ATCs) are a new class of constrained heterocyclic γ-amino acids built around a thiazole ring; these compounds are valuable as design mimics of the secondary structures of proteins such as helices, β-sheets, turns, and β-hairpins. We report herein a short and versatile chemical route to orthogonally protected ATCs. The synthesis is centered on cross-Claisen condensations between N-Fmoc-amino acids and sterically hindered 1,1-dimethylallyl acetate. The optimized conditions are compatible with aliphatic, aromatic, acidic, and basic amino acids. The resulting N-Fmoc-β-keto ester intermediates were engaged in a two-step process to give ATCs in 45–90 % yields. The synthetic protocol provides a highly flexible method for the introduction of a wide variety of lateral chains either on the γ-carbon atom or on the thiazole core of the γ-amino acids.

Domaines

Chimie

Dates et versions

hal-03564162 , version 1 (10-02-2022)

Identifiants

Citer

Loïc Mathieu, Clément Bonnel, Nicolas Masurier, Ludovic Maillard, Jean Martinez, et al.. Cross-Claisen Condensation of N -Fmoc-Amino Acids - A Short Route to Heterocyclic γ-Amino Acids. European Journal of Organic Chemistry, 2015, 2015 (10), pp.2262-2270. ⟨10.1002/ejoc.201500012⟩. ⟨hal-03564162⟩
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