Chemoenzymatic synthesis of optically active 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters |
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| Institution: | 1. Mines Douai, Département Sciences de l’Atmosphère et Génie de l’Environnement (SAGE), 59508 Douai, France;2. Université Lille Nord de France, 59500 Lille, France;3. Groupe de Spectrométrie Moléculaire et Atmosphérique, UMR CNRS 7331, Université de Reims, 51687 Reims, France;4. Université Lille, CNRS, UMR 8522, PC2A-Physicochimie des Processus de Combustion et de l’Atmosphère, F-59000 Lille, France;1. Adam Mickiewicz University in Poznań, Faculty of Chemistry, Umultowska 89b, 61-614 Poznań, Poland;2. AM2N, UMR 5253, ICGM, ENSCM, 8 Rue de l''Ecole Normale, 34296 Montpellier, Cedex 5, France;1. Oles Honchar Dnipro National University, 72 Gagarina Ave., Dnipro 49010, Ukraine;2. SSI «Institute for Single Crystals», National Academy of Sciences of Ukraine, 60 Lenina Ave., Kharkiv 61001, Ukraine;1. LASOL, CCQFA, Universidade Federal de Pelotas—UFPel, PO Box 354, 96010-900 Pelotas, RS, Brazil;2. Grupo de Pesquisa em Neurobiotecnologia—GPN, CDTec, Universidade Federal de Pelotas, UFPel, Pelotas, RS, Brazil |
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| Abstract: | Enantiomerically pure 4-methyl-tetrahydro-5-oxo-2-furancarboxylic acids and esters are prepared by enzymatic resolution of the chiral racemic esters. Their stereochemistry as well as their absolute configurations have been established by chemical correlation. The influence of the alkoxycarbonyl group at C-2 and that of the methyl group at C-4 on the sign of the Cotton effect in their CD spectra have been investigated. Formation of enantiomerically pure hydroxydiesters, precursors of the above-mentioned γ-lactones, by baker’s yeast reduction of the corresponding ketodiesters was unsatisfactory. |
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