Green Strategies for the Preparation of Enantiomeric 5–8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis |
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| Authors: | Sayeh Shahmohammadi,Tü nde Faragó ,Má rta Palkó ,Enikő Forró |
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| Affiliation: | 1.Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, H-6720 Szeged, Hungary; (S.S.); (T.F.); (M.P.);2.MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Hungary |
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| Abstract: | Candida antarctica lipase B-catalyzed hydrolysis of carbocyclic 5–8-membered cis β-amino esters was carried out in green organic media, under solvent-free and ball-milling conditions. In accordance with the high enantioselectivity factor (E > 200) observed in organic media, the preparative-scale resolutions of β-amino esters were performed in tBuOMe at 65 °C. The unreacted β-amino ester enantiomers (1R,2S) and product β-amino acid enantiomers (1S,2R) were obtained with modest to excellent enantiomeric excess (ee) values (ees > 62% and eep > 96%) and in good chemical yields (>25%) in one or two steps. The enantiomers were easily separated by organic solvent/H2O extraction. |
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| Keywords: | green strategies, enzymatic resolution, enantioselective hydrolysis, β -amino acid, ball milling |
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