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

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...

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Bibliographic Details
Published in:Molecules
Main Authors: Sayeh Shahmohammadi, Tünde Faragó, Márta Palkó, Enikő Forró
Format: Article in Journal/Newspaper
Language:English
Published: MDPI AG 2022
Subjects:
green strategies
enzymatic resolution
enantioselective hydrolysis
β-amino acid
ball milling
Organic chemistry
QD241-441
Antarc*
Antarctica
Online Access:https://doi.org/10.3390/molecules27082600
https://doaj.org/article/2c45d39aa7a94924af221179d2fe2163
Description
Summary: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 t BuOMe at 65 °C. The unreacted β-amino ester enantiomers (1 R ,2 S ) and product β-amino acid enantiomers (1 S ,2 R ) were obtained with modest to excellent enantiomeric excess ( ee ) values ( ee s > 62% and ee p > 96%) and in good chemical yields (>25%) in one or two steps. The enantiomers were easily separated by organic solvent/H 2 O extraction.

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