Back to Search Start Over

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

Authors :
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
Université de Sfax - University of Sfax
Source :
SYNTHESIS, SYNTHESIS, Georg Thieme Verlag, 2016, 48 (06), pp.906-916. ⟨10.1055/s-0035-1560404⟩
Publication Year :
2016
Publisher :
Georg Thieme Verlag KG, 2016.

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.

Details

ISSN :
1437210X and 00397881
Volume :
48
Database :
OpenAIRE
Journal :
Synthesis
Accession number :
edsair.doi.dedup.....2a57041d540e490904a40b0202944563
Full Text :
https://doi.org/10.1055/s-0035-1560404