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

A facile chemoenzymatic approach to chiral non-racemic beta-alkyl-gamma-amino acids and 2-alkylsuccinic acids.A concise synthesis of (S)-(+)-Pregabalin

FELLUGA, FULVIA;PITACCO, GIULIANA;VALENTIN, ENNIO;
2008-01-01

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
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/1807152
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