Abstract
A continuous-flow procedure for the synthesis of β-amino acid esters has been developed via lipase-catalyzed Michael reaction of various aromatic amines with acrylates. Lipase TL IM from Thermomyces lanuginosus was first used to catalyze Michael addition reaction of aromatic amines. Compared with other methods, the salient features of this work include green reaction conditions (methanol as reaction medium), short residence time (30 min), readily available catalyst and a reaction process that is easy to control. This enzymatic synthesis of β-amino acid esters performed in continuous-flow microreactors is an innovation that provides a new strategy for the fast biotransformation of β-amino acid esters.
Highlights
Introduction βAmino acid ester derivatives have been widely found in biologically active molecules, many of which possess useful biological activities [1,2,3,4,5,6]. β-Amino acid esters have been used to construct peptidomimetic oligomers, which are of high interest in medicinal chemistry [7,8]
We explored the scope and limitation of this continuous flow methodology for β-amino or methyl acrylate, the target product 3a underwent a second Michael addition reaction, which acid ester synthesis catalyzed by lipase TL IM from Thermomyces lanuginosus
We explored the scope and limitation of this continuous flow methodology for we explored the scope and limitation of this continuous flow methodology for β-amino acid ester synthesis catalyzed by lipase
Summary
Introduction βAmino acid ester derivatives have been widely found in biologically active molecules, many of which possess useful biological activities (e.g., anticancer, antiviral, antibacterial, antifungal, antipsychotics) [1,2,3,4,5,6]. β-Amino acid esters have been used to construct peptidomimetic oligomers, which are of high interest in medicinal chemistry [7,8]. Β-amino acid esters based on aromatic amines are important intermediates for the effective synthesis of urease inhibitors, which can be used in the treatment of Helicobacter pylori infection [9]. Due to these widespread applications in pharmacy and materials science, the development of synthesis methods of β-amino acid esters has become a hot topic in the chemical field. In order to avoid such problems, various transition-metal catalysts have been developed and used to efficiently catalyze the Michael addition to synthesize β-amino acid esters [12,13,14,15,16,17]. Desired results were obtained, the use of metal catalysts and expensive ligands are still shortcomings for the practical utility
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