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

来源：

CHIRALITY | 2020年 / 32卷 / 01期

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

页码：64 / 72

页数：9

共 49 条

[11]

Evans D.A., 1999, COMPREHENSIVE ASSYME, V3, P1177

[12] Polystyrene-supported organocatalysts for α-selenenylation and Michael reactions A common post-modification approach for catalytic differentiation [J].

Giacalone, Francesco ;

Gruttadauria, Michelangelo ;

Agrigento, Paola ;

Campisciano, Vincenzo ;

Noto, Renato .

CATALYSIS COMMUNICATIONS, 2011, 16 (01) :75-80

[13] Diarylprolinol silyl ether as catalyst of an exo-selective, enantioselective Diels-Alder reaction [J].

Gotoh, Hiroaki ;

Hayashi, Yujiro .

ORGANIC LETTERS, 2007, 9 (15) :2859-2862

[14] The development of highly active acyclic chiral hydrazides for asymmetric iminium ion organocatalysis [J].

Gould, Eoin ;

Lebl, Tomas ;

Slawin, Alexandra M. Z. ;

Reid, Mark ;

Davies, Tony ;

Smith, Andrew D. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (45) :7877-7892

[15] Poly(methylhydrosiloxane)-supported chiral imidazolinones: new versatile, highly efficient and recyclable organocatalysts for stereoselective Diels-Alder cycloaddition reactions [J].

Guizzetti, Stefania ;

Benaglia, Maurizio ;

Siegel, Jay S. .

CHEMICAL COMMUNICATIONS, 2012, 48 (26) :3188-3190

[16] Immobilization of MacMillan Imidazolidinone as Mac-SILC and its Catalytic Performance on Sustainable Enantioselective Diels-Alder Cycloaddition [J].

Hagiwara, Hisahiro ;

Kuroda, Toshihiro ;

Hoshi, Takashi ;

Suzuki, Toshio .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (05) :909-916

[17] Design of main-chain polymers of chiral imidazolidinone for asymmetric organocatalysis application [J].

Haraguchi, Naoki ;

Kiyono, Hitomi ;

Takemura, Yu ;

Itsuno, Shinichi .

CHEMICAL COMMUNICATIONS, 2012, 48 (33) :4011-4013

[18] Novel polymer-supported organocatalyst via ion exchange reaction: facile immobilization of chiral imidazolidin-4-one and its application to Diels-Alder reaction [J].

Haraguchi, Naoki ;

Takemura, Yu ;

Itsuno, Shinichi .

TETRAHEDRON LETTERS, 2010, 51 (08) :1205-1208

[19]

Hayashi Y, 2002, CYCLOADDITION REACTIONS IN ORGANIC SYNTHESIS, P5

[20] Asymmetric Diels-Alder reactions of α,β-unsaturated aldehydes catalyzed by a diarylprolinol silyl ether salt in the presence of water [J].

Hayashi, Yujiro ;

Samanta, Sampak ;

Gotoh, Hiroaki ;

Ishikawa, Hayato .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (35) :6634-6637

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