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Room Temperature Ionic Liquids in the Kinetic Resolution of Adrenaline‐Type Aminoethanols by Burkholderia cepacia Lipase under Normal and Microwave Conditions
Author(s) -
Lundell Katri,
Kurki Toni,
Lindroos Maria,
Kanerva Liisa T.
Publication year - 2005
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200505049
Subject(s) - chemistry , ionic liquid , acylation , kinetic resolution , lipase , burkholderia , organic chemistry , substrate (aquarium) , catalysis , enzyme , enantioselective synthesis , oceanography , geology , biology , bacteria , genetics
Abstract The lipase PS‐C II (lipase from Burkholderia cepacia immobilized on ceramic particles)‐catalyzed acylations of N ‐acylated 2‐amino‐1‐phenylethanol ( rac‐ 1 ) and N ‐acylated norphenylephrine ( rac‐ 2 ) have been studied in imidazolium‐ and pyridinium‐based ionic liquids, in tert ‐butyl methyl ether (TBME) and in their mixtures. Enzymatic chemo‐ and enantioselectivities in the presence of hydrophobic EMIM⋅NTf 2 and hydrophilic EMIM⋅BF 4 have been studied in more detail using high substrate concentrations. The preparative‐scale kinetic resolution of rac‐ 1 and rac‐ 2 (both 0.45 M) with vinyl butanoate in the mixture of EMIM⋅NTf 2 with TBME (2 : 1) took 9 and 27 hours, respectively. Microwave‐assisted acylation of rac‐ 1 and rac‐ 2 in the presence of EMIM⋅NTf 2 proceeded similarly to the reactions under normal conditions.