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