Green Strategies for the Preparation of Enantiomeric 5-8-Membered Carbocyclic β-Amino Acid Derivatives through CALB-Catalyzed Hydrolysis.

Autor: Shahmohammadi S; Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, H-6720 Szeged, Hungary.; MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, H-6720 Szeged, Hungary., Faragó T; Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, H-6720 Szeged, Hungary., Palkó M; Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, H-6720 Szeged, Hungary., Forró E; Institute of Pharmaceutical Chemistry, Interdisciplinary Excellence Center, Faculty of Pharmacy, University of Szeged, H-6720 Szeged, Hungary.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2022 Apr 18; Vol. 27 (8). Date of Electronic Publication: 2022 Apr 18.
DOI: 10.3390/molecules27082600
Abstrakt: 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.
Databáze: MEDLINE
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