Lipase-catalyzed enantioselective reaction of amines with carboxylic acids under reduced pressure in non-solvent system and in ionic liquids

被引:65
作者
Irimescu, R [1 ]
Kato, K [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Ceram Res Inst, Biofunct Ceram Grp, Moriyama Ku, Nagoya, Aichi 4638560, Japan
关键词
enzymatic amide synthesis; ionic liquids; kinetic resolution; lipase; non-solvent reaction system; primary amine;
D O I
10.1016/j.tetlet.2003.10.210
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lipase-catalyzed enantioselective acylation of I-phenylethylamine and 2-phenyl-1-propylamine was performed by reacting the amines with carboxylic acids in a non-solvent system or in ionic liquids as reaction media. The reaction equilibrium was shifted toward amide synthesis by the removal of formed water under reduced pressure. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:523 / 525
页数:3
相关论文
共 13 条
[1]  
Beckwith A. L. J., 1970, CHEM AMIDES, P105
[2]  
BORNSCHEUER UT, 1999, HYDROLASES ORGANIC S, P103
[3]   CAL-B-catalyzed resolution of some pharmacologically interesting β-substituted isopropylamines [J].
González-Sabín, J ;
Gotor, V ;
Rebolledo, F .
TETRAHEDRON-ASYMMETRY, 2002, 13 (12) :1315-1320
[4]   Enzymatic kinetic resolution of secondary alcohols by esterification with FA under vacuum [J].
Irimescu, R ;
Saito, T ;
Kato, K .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2003, 80 (07) :659-663
[5]   Efficient lipase-catalyzed enantioselective acylation under reduced pressure conditions in an ionic liquid solvent system [J].
Itoh, T ;
Akasaki, E ;
Nishimura, Y .
CHEMISTRY LETTERS, 2002, (02) :154-155
[6]   Lipase-catalyzed enantioselective acylation in the ionic liquid solvent system: Reaction of enzyme anchored to the solvent [J].
Itoh, T ;
Akasaki, E ;
Kudo, K ;
Shirakami, S .
CHEMISTRY LETTERS, 2001, (03) :262-263
[7]   Lipase-catalyzed reactions in ionic liquids [J].
Lau, RM ;
van Rantwijk, F ;
Seddon, KR ;
Sheldon, RA .
ORGANIC LETTERS, 2000, 2 (26) :4189-4191
[8]   THE PENT-4-ENOYL GROUP - A NOVEL AMINE-PROTECTING GROUP THAT IS READILY CLEAVED UNDER MILD CONDITIONS [J].
MADSEN, R ;
ROBERTS, C ;
FRASERREID, B .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7920-7926
[9]   SYNTHESIS OF N-LAURYLOLEYLAMIDE BY THE MUCOR MIEHEI LIPASE IN AN ORGANIC MEDIUM [J].
MONTET, D ;
PINA, M ;
GRAILLE, J ;
RENARD, G ;
GRIMAUD, J .
FETT WISSENSCHAFT TECHNOLOGIE-FAT SCIENCE TECHNOLOGY, 1989, 91 (01) :14-18
[10]   Kinetic resolutions of amine and thiol analogues of secondary alcohols catalyzed by the Candida antarctica lipase B [J].
Ohrner, N ;
Orrenius, C ;
Mattson, A ;
Norin, T ;
Hult, K .
ENZYME AND MICROBIAL TECHNOLOGY, 1996, 19 (05) :328-331