- Mechanochemical enzymatic resolution of N-benzylated-β3-amino esters
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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.
- Pérez-Venegas, Mario,Reyes-Rangel, Gloria,Neri, Adrián,Escalante, Jaime,Juaristi, Eusebio
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p. 1728 - 1734
(2017/09/27)
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- Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A
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The enantioselectivities for the reactions of aliphatic β-substituted β-amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E = 70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates.
- Gedey, Szilvia,Liljeblad, Arto,Lazar, Laszlo,Fueloep, Ferenc,Kanerva, Liisa T.
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p. 105 - 110
(2007/10/03)
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