Efficient catalytic synthesis of optically active cyclic carbonates via coupling reaction of epoxides and carbon dioxide

被引:67
作者
Chen, Shu-Wei [1 ]
Kawthekar, Rahul B. [1 ]
Kim, Geon-Joong [1 ]
机构
[1] Inha Univ, Dept Chem Engn, Inchon 402751, South Korea
关键词
chiral cobalt salen; epoxides; Lewis acid; resolution;
D O I
10.1016/j.tetlet.2006.11.014
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral Co(salen) complexes bearing the Lewis acid of group 13 can efficiently catalyze the reactions of carbon dioxide with epoxides in the presence of catalytic amounts of alkali metal salts, quaternary ammonium halide or ionic liquids. They exhibited excellent activity for producing enantiomerically enriched cyclic carbonates. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:297 / 300
页数:4
相关论文
共 23 条
[1]   Selective plasma hydrolysis of glucocorticoid γ-lactones and cyclic carbonates by the enzyme paraoxonase:: An ideal plasma inactivation mechanism [J].
Biggadike, K ;
Angell, RM ;
Burgess, CM ;
Farrell, RM ;
Hancock, AP ;
Harker, AJ ;
Irving, WR ;
Ioannou, C ;
Procopiou, PA ;
Shaw, RE ;
Solanke, YE ;
Singh, OMP ;
Snowden, MA ;
Stubbs, RJ ;
Walton, S ;
Weston, HE .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (01) :19-21
[2]   Cyclic carbonate formation from carbon dioxide and oxiranes in tetrabutylammonium halides as solvents and catalysts [J].
Caló, V ;
Nacci, A ;
Monopoli, A ;
Fanizzi, A .
ORGANIC LETTERS, 2002, 4 (15) :2561-2563
[3]   Catalysts for the reactions of epoxides and carbon dioxide [J].
Darensbourg, DJ ;
Holtcamp, MW .
COORDINATION CHEMISTRY REVIEWS, 1996, 153 :155-174
[4]   CATALYTIC ACTIVITY OF VARIOUS SALTS IN THE REACTION OF 2,3-EPOXYPROPYL PHENYL ETHER AND CARBON-DIOXIDE UNDER ATMOSPHERIC-PRESSURE [J].
KIHARA, N ;
HARA, N ;
ENDO, T .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (23) :6198-6202
[5]   A novel and effective Ni complex catalyst system for the coupling reactions of carbon dioxide and epoxides [J].
Li, FW ;
Xia, CG ;
Xu, LW ;
Sun, W ;
Chen, GX .
CHEMICAL COMMUNICATIONS, 2003, (16) :2042-2043
[6]   Asymmetric catalysis with CO2:: Direct synthesis of optically active propylene carbonate from racemic epoxides [J].
Lu, XB ;
Liang, B ;
Zhang, YJ ;
Tian, YZ ;
Wang, YM ;
Bai, CX ;
Wang, H ;
Zhang, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (12) :3732-3733
[7]   ENZYME-MEDIATED ENANTIOSELECTIVE HYDROLYSIS OF CYCLIC CARBONATES [J].
MATSUMOTO, K ;
FUWA, S ;
KITAJIMA, H .
TETRAHEDRON LETTERS, 1995, 36 (36) :6499-6502
[8]   Chiral (salen)CoIII catalyst for the synthesis of cyclic carbonates [J].
Paddock, RL ;
Nguyen, ST .
CHEMICAL COMMUNICATIONS, 2004, (14) :1622-1623
[9]   Chemical CO2 fixation:: Cr(III) salen complexes as highly efficient catalysts for the coupling of CO2 and epoxides [J].
Paddock, RL ;
Nguyen, ST .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (46) :11498-11499
[10]   Cycloaddition of carbon dioxide to propylene oxide catalyzed by ionic liquids [J].
Peng, JJ ;
Deng, YQ .
NEW JOURNAL OF CHEMISTRY, 2001, 25 (04) :639-641