1. A Short Access to Symmetrically α,α-Disubstituted α-Amino Acids from Acyl Cyanohydrins
- Author
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Florian Rouzier, Fabien Boeda, Julien Caillé, Philippe Bertus, Morwenna S. M. Pearson-Long, Houcine Ammar, Fatma Boukattaya, Institut des Molécules et Matériaux du Mans (IMMM), Le Mans Université (UM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Faculté des Sciences de Sfax, and Université de Sfax - University of Sfax
- Subjects
chemistry.chemical_classification ,amino acids ,Grignard reagents ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Chemistry ,Stereochemistry ,Organic Chemistry ,Nucleophilic acyl substitution ,solvent effects ,010402 general chemistry ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Amino acid ,Acylation ,Reagent ,Moiety ,cyanohydrins ,nitriles ,Solvent effects ,Chemoselectivity - Abstract
International audience; 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.
- Published
- 2016