scholarly journals Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters

2017 ◽  
Vol 13 ◽  
pp. 1728-1734 ◽  
Author(s):  
Mario Pérez-Venegas ◽  
Gloria Reyes-Rangel ◽  
Adrián Neri ◽  
Jaime Escalante ◽  
Eusebio Juaristi
Keyword(s):  
Amino Acids ◽  
Ball Milling ◽  
Present Article ◽  
Candida Antarctica ◽  
Lipase B ◽  
Enzymatic Resolution ◽  
Amino Esters ◽  
Enantioselective Reactions

The use of mechanochemistry to carry out enantioselective reactions has been explored in the last ten years with excellent results. Several chiral organocatalysts and even enzymes have proved to be resistant to milling conditions, which allows for rather efficient enantioselective transformations under ball-milling conditions. The present article reports the first example of a liquid-assisted grinding (LAG) mechanochemical enzymatic resolution of racemic β3-amino esters employing Candida antarctica lipase B (CALB) to afford highly valuable enantioenriched N-benzylated-β3-amino acids in good yields. Furthermore the present protocol is readily scalable.

Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters

2002 ◽  
Vol 80 (6) ◽  
pp. 565-570 ◽  
Author(s):  
Szilvia Gedey ◽  
Arto Liljeblad ◽  
László Lázár ◽  
Ferenc Fülöp ◽  
Liisa T Kanerva
Keyword(s):  
Key Words ◽  
Candida Antarctica ◽  
Diisopropyl Ether ◽  
The Other ◽  
Candida Antarctica Lipase B ◽  
Candida Antarctica Lipase ◽  
Structural Effects ◽  
Lipase B ◽  
Amino Esters ◽  
Catalyzed Reactions

The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method. Key words: lipase, interesterification, acylation, alcoholysis, resolution, β-amino esters.

ChemInform Abstract: Structural Effects on Chemo- and Enantio-Selectivity of Candida antarctica Lipase B - Resolution of β-Amino Esters.

ChemInform ◽  
2010 ◽  
Vol 33 (46) ◽  
pp. no-no
Author(s):  
Szilvia Gedey ◽  
Arto Liljeblad ◽  
Laszlo Lazar ◽  
Ferenc Fueloep ◽  
Liisa T. Kanerva
Keyword(s):  
Candida Antarctica ◽  
Candida Antarctica Lipase B ◽  
Candida Antarctica Lipase ◽  
Structural Effects ◽  
Lipase B ◽  
Amino Esters

Enzymatic Resolution of β-Amino Methyl Esters using Lipase B from Candida antarctica.

2008 ◽  
Author(s):  
Jaime Escalante ◽  
Enrique Díaz-Herrera ◽  
Eusebio Juaristi
Keyword(s):  
Methyl Esters ◽  
Candida Antarctica ◽  
Lipase B ◽  
Enzymatic Resolution

Enzymatic resolution of racemic secondary alcohols by lipase B from Candida antarctica

2000 ◽  
Vol 77 (10) ◽  
pp. 1015-1019 ◽  
Author(s):  
Ramesh N. Patel ◽  
Amit Banerjee ◽  
Venkata Nanduri ◽  
Animesh Goswami ◽  
F. T. Comezoglu
Keyword(s):  
Candida Antarctica ◽  
Secondary Alcohols ◽  
Lipase B ◽  
Enzymatic Resolution

Enzymatic resolution of N-protected-β3-amino methyl esters, using lipase B from Candida antarctica

2005 ◽  
Vol 16 (3) ◽  
pp. 629-634 ◽  
Author(s):  
Patricia Flores-Sánchez ◽  
Jaime Escalante ◽  
Edmundo Castillo
Keyword(s):  
Methyl Esters ◽  
Candida Antarctica ◽  
Lipase B ◽  
Enzymatic Resolution

Exogenous Directing Group Free, Ligand-Enabled gamma-C(sp3)–H Arylation of Free Primary Aliphatic Amines and α-Amino Esters

2019 ◽  
Author(s):  
Yongzheng Ding ◽  
Shuai Fan ◽  
Xiaoxi Chen ◽  
yuzhen gao ◽  
Gang Li
Keyword(s):  
Amino Acids ◽  
Large Scale ◽  
Free Ligand ◽  
Aliphatic Amines ◽  
Rapid Synthesis ◽  
Amino Esters ◽  
Directing Group ◽  
Large Scale Synthesis ◽  
Primary Aliphatic Amines

A Pdᴵᴵ-catalyzed, ligand-enabled gamma-C(sp3)–H arylation of free primary aliphatic amines and amino esters without using an exogenous directing group is reported. This reaction is compatible with unhindered free aliphatic amines, and it is also be applicable to the rapid synthesis of biologically and synthetically valuable unnatural α-amino acids. Large scale synthesis is also feasible using this method.<br>

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