1. A facile chemoenzymatic approach to chiral non-racemic β-alkyl-γ-amino acids and 2-alkylsuccinic acids. A concise synthesis of (S)-(+)-Pregabalin
- Author
-
Cesare Daniele Venneri, Ennio Valentin, Fulvia Felluga, Giuliana Pitacco, Felluga, Fulvia, Pitacco, Giuliana, Valentin, Ennio, and Venneri, C. D.
- Subjects
chiral nitroesters ,Hydrochloride ,enzymatic hydrolysis ,gamma amino acids ,GABA analogs ,gamma lactams ,chiral nitroester ,GABA analog ,Catalysis ,Kinetic resolution ,Inorganic Chemistry ,chemistry.chemical_compound ,Organic chemistry ,Physical and Theoretical Chemistry ,Alkyl ,chemistry.chemical_classification ,enzymatic hydrolysi ,gamma amino acid ,Organic Chemistry ,Amino acid ,Nef reaction ,Enzyme ,chemistry ,Succinic acid ,Derivative (chemistry) - Abstract
Both enantiomerically pure antipodes of GABA analogues were prepared as hydrochloride salts, by enzymatic kinetic resolution of their precursors ethyl 2-(nitromethyl)alkanoates. These latter compounds can be easily transformed into enantiomerically pure 2-alkylsuccinic acids by a Nef reaction followed by oxidation. Interestingly, this reaction was particularly easy for the neopentyl derivative ( S )-(+)- 7d , which underwent conversion into its corresponding succinic acid derivative ( S )-(−)- 8d in buffered solution. The absolute configurations of the main compounds of interest involved are given, together with their CD spectra.
- Published
- 2008
- Full Text
- View/download PDF