Synthesis of new optically pure tetrabromobenzotriazole derivatives via lipase-catalyzed transesterification
Adam M. Wawro , Monika Wielechowska , Maria Bretner
AbstractAn efficient and convenient approach to synthesis of new, enantiopure hydroxyalkyl derivatives of 4,5,6,7-tetrabromo-1H-benzotriazole (TBBt) has been developed. Prochiral ketones synthesized through alkylation of TBBt were reduced to racemic secondary alcohols, which were separated by kinetic resolution carried out by lipase-catalyzed transesterification. After optimization of solvent, lipase and acyl donor group, the highest enantioselectivity factor (E \> 200) and optical purity of the products (\>99\%) was achieved with lipase Amano AK from Pseudomonas fluorescens in tert-butyl methyl ether.
|Journal series||Journal of Molecular Catalysis B-Enzymatic, ISSN 1381-1177|
|Publication size in sheets||0.5|
|Keywords in English||Enzymatic transesterification, Inhibitors of casein kinase CK2, Lipase, Tetrabromobenzotriazole derivatives|
|ASJC Classification||; ; ;|
|Score|| = 30.0, 17-08-2020, ArticleFromJournal|
= 30.0, 17-08-2020, ArticleFromJournal
|Publication indicators||= 7; = 5; = 3.0; : 2013 = 1.378; : 2013 = 2.745 (2) - 2013=2.786 (5)|
|Citation count*||3 (2015-10-29)|
* presented citation count is obtained through Internet information analysis and it is close to the number calculated by the Publish or Perish system.