scholarly journals Towards sustainable kinetic resolution, a combination of bio-catalysis, flow chemistry and bio-based solvents

2018 ◽  
Vol 20 (1) ◽  
pp. 136-140 ◽  
Author(s):  
Andree Iemhoff ◽  
James Sherwood ◽  
Con R. McElroy ◽  
Andrew J. Hunt

The esterification of 2-phenylpropionic acid was investigated as a model system for enzyme catalysed (CALB, Novozyme 435) reactions in bio-based solvents.

2014 ◽  
Vol 68 (6) ◽  
Author(s):  
Vladimír Mastihuba ◽  
Pavel Čepec ◽  
Silvia Vlčková ◽  
Erika Farkašová ◽  
Mária Mastihubová ◽  
...  

AbstractTwo lipases, Novozyme 435 (lipase B from Candida Antarctica) and Lipozyme TL IM (Thermomyces lanuginosus) were used successfully for the kinetic resolution of racemic 1-(2-furyl)-3-pentanol, the key intermediate in synthesis of the bark beetle pheromone, chalcogran. The desired S-(+)-enantiomer was prepared in enantiomeric excesses higher than 98 % and with yields of 26.3 % and 32.5 %, respectively. Methyl tert-butyl ether and vinyl acetate were found to be the best reaction media and the acetyl donor to achieve fast and effective resolution.


Synlett ◽  
2019 ◽  
Vol 30 (13) ◽  
pp. 1555-1560 ◽  
Author(s):  
Siegfried Harrer ◽  
Mark D. Greenhalgh ◽  
Rifahath M. Neyyappadath ◽  
Andrew D. Smith

The isothiourea-catalysed acylative kinetic resolution of a range of acyclic (±)-1,2-diols using 1 mol% of catalyst under operationally simple conditions is reported. Significantly, the bifunctional nature of (±)-1,2-diols was exploited in a sequential double kinetic resolution, in which both kinetic resolutions operate synergistically to provide access to highly enantioenriched products. The principles that underpin this process are discussed, and selectivity factors for the individual kinetic resolution steps are reported in a model system.


Tetrahedron ◽  
2015 ◽  
Vol 71 (29) ◽  
pp. 4738-4744 ◽  
Author(s):  
Xiaojian Zhou ◽  
Daijun Zheng ◽  
Baodong Cui ◽  
Wenyong Han ◽  
Yongzheng Chen

2004 ◽  
Vol 15 (19) ◽  
pp. 3117-3122 ◽  
Author(s):  
Cristiano Raminelli ◽  
João V. Comasseto ◽  
Leandro H. Andrade ◽  
André L.M. Porto

SynOpen ◽  
2018 ◽  
Vol 02 (02) ◽  
pp. 0192-0199 ◽  
Author(s):  
A. Grollmisch ◽  
U. Kragl ◽  
J. Großeheilmann

Enzyme immobilization in polymerized ionic liquids (PILs) promises to be a versatile tool for simple recovery and reuse of catalysts. In this study, a raw extract of CalB was encapsulated in poly(VEImBr) and assessed with respect to solvent, temperature, amount of enzyme, leaching behavior, and reusability on the example of the kinetic resolution of rac-1-phenylethanol with vinyl acetate. This immobilization method increased the enzyme activity of the CalB raw extract in comparison to the non-immobilized enzyme. The desired product was synthesized with high enantiomeric excess (ee) and no leaching of active enzyme was observed in the experiments. The immobilization method was compared to Novozyme 435 and Lipozyme RM IM, as commercially available immobilisates. Nonpolar solvents, including n-heptane and n-dodecane, proved to be the best reaction solvents, showing nearly full conversion and high catalytic activities. The encapsulated ­lipase was easily recovered from the reaction mixture and reused for ten cycles.


ChemInform ◽  
2005 ◽  
Vol 36 (10) ◽  
Author(s):  
Cristiano Raminelli ◽  
Joao V. Comasseto ◽  
Leandro H. Andrade ◽  
Andre L. M. Porto

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