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EnglishBoth 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
| Titolo: | A facile chemoenzymatic approach to chiral non-racemic beta-alkyl-gamma-amino acids and 2-alkylsuccinic acids.A concise synthesis of (S)-(+)-Pregabalin |
| Autori: | |
| Data di pubblicazione: | 2008 |
| Rivista: | |
| 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 |
| Handle: | http://hdl.handle.net/11368/1807152 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1016/j.tetasy.2008.03.014 |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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