Chiral Imidazolidin-4-one with catalytic amount of Dicationic ionic liquid act as a recoverable and reusable Organocatalyst for asymmetric Diels-Alder reaction

被引:10
作者
Deepa [1 ]
Yadav, Geeta Devi [1 ]
Chaudhary, Pooja [1 ]
Aalam, Mohd Jubair [1 ]
Meena, Dhan Raj [1 ]
Singh, Surendra [1 ]
机构
[1] Univ Delhi, Dept Chem, North Campus, Delhi 110007, India
关键词
Crotonaldehyde; Cyclopentadiene; Dicationic ionic liquid; Diels-Alder reaction; modified MacMillan catalyst; DIARYLPROLINOL SILYL ETHER; IMMOBILIZATION; EFFICIENT; DESIGN; CASH;
D O I
10.1002/chir.23137
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Imidazolidin-4-one is used as a recoverable organocatalyst for the asymmetric Diels-Alder reaction in the presence of catalytic amount of dicationic ionic liquid and trifluoroacetic acid as a co-catalyst. The Diels-Alder reaction between model substrate cyclopentadiene and crotonaldehyde gave the product in 95% conversion and 87% ee of the endo-product. The catalyst was shown better reusability when the 20 mol% of dicationic ionic liquid was used and catalyst was reused upto 5 cycles, conversion remains upto 3 recycles but ee of endo-9 was slightly droped.
引用
收藏
页码:64 / 72
页数:9
相关论文
共 49 条
[1]   New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].
Ahrendt, KA ;
Borths, CJ ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244
[2]   Applications of asymmetric organocatalysis in medicinal chemistry [J].
Aleman, Jose ;
Cabrera, Silvia .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :774-793
[3]  
Benaglia M, 2002, ADV SYNTH CATAL, V344, P149, DOI 10.1002/1615-4169(200202)344:2<149::AID-ADSC149>3.0.CO
[4]  
2-U
[5]   Synthesis of new chiral cyclic 1,2-diamines and their evaluation as catalysts for enantioselective Diels-Alder reactions [J].
Biaggi, Cinzia ;
Benaglia, Maurizio ;
Rossi, Sergio ;
Proto, Stefano ;
Annunziata, Rita .
TETRAHEDRON LETTERS, 2007, 48 (48) :8521-8525
[6]   Synthesis of MacMillan catalyst modified with ionic liquid as a recoverable catalyst for asymmetric Diels-Alder reaction [J].
Chauhan, ManMohan Singh ;
Kumar, Pramod ;
Singh, Surendra .
RSC ADVANCES, 2015, 5 (65) :52636-52641
[7]   Asymmetric reduction of ketones catalyzed by α,α-diphenyl-(L)-prolinol modified with imidazolium ionic liquid and BH3•SMe2 as a recoverable catalyst [J].
Chauhan, ManMohan Singh ;
Singh, Surendra .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2015, 398 :184-189
[8]   A recyclable fluorous organocatalyst for Diels-Alder reactions [J].
Chu, Qianli ;
Zhang, Wei ;
Curran, Dennis P. .
TETRAHEDRON LETTERS, 2006, 47 (52) :9287-9290
[9]  
Corey EJ, 2002, ANGEW CHEM INT EDIT, V41, P1650, DOI 10.1002/1521-3773(20020517)41:10<1650::AID-ANIE1650>3.0.CO
[10]  
2-B