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Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2016

A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins

Résumé

A straightforward synthesis of symmetrically α,α-disubstituted α-amino acids is presented. The key step of this process relies on the efficient double addition of Grignard reagents to acyl cyanohydrins to provide N-acyl amino alcohols selectively in good yields. The chemoselectivity of the reaction was modulated by the nature of the acyl moiety. Eleven amino acids were prepared, including the particularly simple divinylglycine, which is not easily accessible by using conventional methods.

Domaines

Chimie organique
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Dates et versions

hal-02132492 , version 1 (17-05-2019)

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Fatma Boukattaya, Julien Caillé, Houcine Ammar, Florian Rouzier, Fabien Boeda, et al.. A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins. Synthesis: Journal of Synthetic Organic Chemistry, 2016, 48 (06), pp.906-916. ⟨10.1055/s-0035-1560404⟩. ⟨hal-02132492⟩
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