Highly enantioselective Michael addition reactions with new trimeric chiral phase transfer catalysts

被引:11
作者
Beneto, Arockiam Jesin [1 ]
Sivamani, Jayaraman [1 ]
Ashokkumar, Veeramanoharan [1 ]
Balasaravanan, Rajendiran [1 ]
Duraimurugan, Kumaraguru [1 ]
Siva, Ayyanar [1 ]
机构
[1] Madurai Kamaraj Univ, Sch Chem, Dept Inorgan Chem, Madurai 625021, Tamil Nadu, India
关键词
ASYMMETRIC ALKYLATIONS; EFFICIENCY; MALONATE; ANIONS; BASE; SALT;
D O I
10.1039/c4nj02395a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
New types of mesitylene based tri-site containing asymmetric quaternary ammonium salts 9a and 9b have been prepared and used as efficient chiral phase transfer catalysts for enantioselective Michael addition reactions between the chalcones and diethylmalonate under mild reaction conditions such as lower concentration of base, catalyst and ultrasonic conditions with very good chemical yields (up to 98%) and ee's (up to 99%).
引用
收藏
页码:3098 / 3104
页数:7
相关论文
共 54 条
[1]   Phase-transfer-catalyzed asymmetric glycolate alkylation [J].
Andrus, MB ;
Hicken, EJ ;
Stephens, JC .
ORGANIC LETTERS, 2004, 6 (13) :2289-2292
[2]  
Berkessel A, 2005, ASYMMETRIC ORGANOCATALYSIS: FROM BIOMIMETIC CONCEPTS TO APPLICATIONS IN ASYMMETRIC SYNTHESIS, P1, DOI 10.1002/3527604677
[3]   Exhaustive removal of anions from aqueous waste via nucleophilic displacement reactions in the presence of phase transfer catalysts [J].
Bielski, R ;
Joyce, PJ .
CATALYSIS COMMUNICATIONS, 2003, 4 (08) :401-404
[4]   Highly Enantioselective Michael Addition of Malonate Derivatives to Enones Catalyzed by an N,N′-Dioxide-Scandium(III) Complex [J].
Chen, Donghui ;
Chen, Zhenling ;
Xiao, Xiao ;
Yang, Zhigang ;
Lin, Lili ;
Liu, Xiaohua ;
Feng, Xiaoming .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (28) :6807-6810
[5]   Highly enantioselective phase transfer catalyzed alkylation of a 3-oxygenated propionic ester equivalent; applications and mechanism [J].
Corey, EJ ;
Bo, YX ;
Busch-Petersen, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :13000-13001
[6]  
Dalko P.I., 2007, ENANTIOSELECTIVE ORG
[7]  
Dehmlow E.V., 1993, PHASE TRANSFER CATAL, DOI DOI 10.1039/b602046a
[8]   Influence of ionic liquids on the phase transfer-catalysed enantioselective Michael reaction [J].
Dere, RT ;
Pal, RR ;
Patil, PS ;
Salunkhe, MM .
TETRAHEDRON LETTERS, 2003, 44 (28) :5351-5353
[9]   EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].
DOLLING, UH ;
DAVIS, P ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447
[10]   Enantioselective alkylations of tributyltin enolates catalyzed by Cr(salen)Cl: Access to enantiomerically enriched all-carbon quaternary centers [J].
Doyle, AG ;
Jacobsen, EN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (01) :62-63