Solvent-free biocatalytic amidation of carboxylic acids

被引:38
作者
Prasad, AK [1 ]
Husain, M
Singh, BK
Gupta, RK
Manchanda, VK
Olsen, CE
Parmar, VS
机构
[1] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 100007, India
[2] GGSIP Univ, Sch Biotechnol, Delhi 110006, India
[3] Bhabha Atom Res Ctr, Div Radiochem, Bombay 400085, Maharashtra, India
[4] Royal Vet & Agr Univ, Dept Chem, DK-1871 Copenhagen, Denmark
关键词
lipase; enantioselective; amidation; bulk reaction; chiral amide;
D O I
10.1016/j.tetlet.2005.04.121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Lipase-catalyzed enantioselective amidation was performed by reacting the racemic amine with aliphatic acids in nonsolvent system. The reaction equilibrium was shifted towards amide synthesis by the removal of water under reduced pressure. This methodology avoids the use of activating agents and hazardous solvents. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4511 / 4514
页数:4
相关论文
共 33 条
[1]   Lipase catalysed synthesis of optically enriched α-haloamides [J].
Azim, A ;
Sharma, SK ;
Olsen, CE ;
Parmar, VS .
BIOORGANIC & MEDICINAL CHEMISTRY, 2001, 9 (05) :1345-1348
[2]   Enantioselective aminolysis of an α-chloroester catalyzed by Candida cylindracea lipase encapsulated in sol-gel silica glass [J].
Badjic, JD ;
Kadnikova, EN ;
Kostic, NM .
ORGANIC LETTERS, 2001, 3 (13) :2025-2028
[3]   Highly efficient and selective biocatalytic acylation studies on triazolylsugars [J].
Bhattacharya, A ;
Prasad, AK ;
Maity, J ;
Himanshu ;
Poonam ;
Olsen, CE ;
Gross, RA ;
Parmar, VS .
TETRAHEDRON, 2003, 59 (51) :10269-10277
[4]   Synthesis of tertiary amines using a polystyrene (REM) resin [J].
Brown, AR ;
Rees, DC ;
Rankovic, Z ;
Morphy, JR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (14) :3288-3295
[5]   CHEMISTRY OF CEPHALOSPORIN ANTIBIOTICS .21. CONVERSION OF PENICILLINS TO CEPHALEXIN [J].
CHAUVETT.RR ;
PENNINGT.PA ;
RYAN, CW ;
COOPER, RDG ;
JOSE, FL ;
WRIGHT, IG ;
VANHEYNI.EM ;
HUFFMAN, GW .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) :1259-&
[6]  
COPALA GM, 1987, ASYMMETRIC SYNTHESIS
[7]  
de Castro MS, 2000, TETRAHEDRON, V56, P1387
[8]  
EVANS DA, 1969, TETRAHEDRON LETT, P1573
[9]  
FEO RJD, 1963, J ORG CHEM, V28, P2915
[10]   Kinetic resolution of (±)-trans- and (±)-cis-2-phenylcyclopentanamine by CALB-catalyzed aminolysis of esters:: the key role of the leaving group [J].
González-Sábin, J ;
Gotor, V ;
Rebolledo, F .
TETRAHEDRON-ASYMMETRY, 2004, 15 (03) :481-488