An efficient biomaterial supported bifunctional organocatalyst (ES-SO3- C5H5NH+) for the synthesis of β-amino carbonyls

被引:35
作者
Verma, Sanny [1 ]
Jain, Suman L. [1 ]
Sain, Bir [1 ]
机构
[1] Indian Inst Petr, Div Chem Sci, Mohkampur 248005, Dehradun, India
关键词
AZA-MICHAEL REACTION; CATALYZED CONJUGATE ADDITION; ALPHA; BETA-ETHYLENIC COMPOUNDS; ASYMMETRIC ORGANOCATALYSIS; ACID; LIQUID; SYSTEM; ESTERS;
D O I
10.1039/c0ob00965b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A biomaterial supported organocatalyst, readily synthesized by the reaction of chemically modified sulfonic group containing expanded corn starch with pyridine exhibited excellent catalytic activity for the synthesis of beta-amino carbonyls in excellent yields via aza-Michael addition of amines to electron deficient alkenes. A remarkable enhancement in the reaction rates was observed with the prepared bifunctional organocatalyst in comparison to the either starch grafted sulfonic acid or the corresponding homogeneous pyridinium p-toluenesulfonate.
引用
收藏
页码:2314 / 2318
页数:5
相关论文
共 44 条
[1]  
ASLAM UM, 2010, RENEWABLE ENERGY RES
[2]   Conjugate addition of amines to α,β-enones promoted by CeCl3•7H2O-NaI system supported in silica gel [J].
Bartoli, G ;
Bosco, M ;
Marcantoni, E ;
Petrini, M ;
Sambri, L ;
Torregiani, E .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (26) :9052-9055
[3]   CHEMOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF BETA-ENAMINO ESTERS - A CONVENIENT SYNTHESIS OF BOTH CIS-GAMMA-AMINO AND TRANS-GAMMA-AMINO ALCOHOLS AND BETA-AMINO ESTERS [J].
BARTOLI, G ;
CIMARELLI, C ;
MARCANTONI, E ;
PALMIERI, G ;
PETRINI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5328-5335
[4]   Polymer-supported organic catalysts [J].
Benaglia, M ;
Puglisi, A ;
Cozzi, F .
CHEMICAL REVIEWS, 2003, 103 (09) :3401-3429
[5]  
Benaglia M., 2009, RECOVERABLE RECYCLAB
[6]  
Biermann U, 2000, ANGEW CHEM INT EDIT, V39, P2206, DOI 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO
[7]  
2-P
[8]  
Biermann U, 2000, ANGEW CHEM, V112, P2292
[9]   Asymmetric synthesis of beta-amino acids and alpha-substituted beta-amino acids [J].
Cardillo, G ;
Tomasini, C .
CHEMICAL SOCIETY REVIEWS, 1996, 25 (02) :117-&
[10]   Boric acid: a novel and safe catalyst for aza-Michael reactions in water [J].
Chaudhuri, MK ;
Hussain, S ;
Kantam, ML ;
Neelima, B .
TETRAHEDRON LETTERS, 2005, 46 (48) :8329-8331