A Magnetoclick Imidazolidinone Nanocatalyst for Asymmetric 1,3-Dipolar Cycloadditions

被引:32
作者
Pagoti, Sreenivasarao [1 ]
Dutta, Debasish [1 ]
Dash, Jyotirmayee [1 ]
机构
[1] Indian Assoc Cultivat Sci Jadavpur, Dept Organ Chem, Kolkata 700032, India
关键词
asymmetric catalysis; click chemistry; 1; 3-dipolar cycloaddition; enantioselectivity; green chemistry; magnetic separation; nano catalyst; DIELS-ALDER REACTIONS; ORGANIC CATALYSIS; CHIRAL IMIDAZOLIDIN-4-ONE; MAGNETIC NANOPARTICLES; MICHAEL REACTION; STRATEGIES; ORGANOCATALYSTS; IMMOBILIZATION; FUNCTIONALIZATION; PERFORMANCE;
D O I
10.1002/adsc.201300624
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A 1,3-dipolar azide-alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3-dipolar cycloaddition between nitrones and ,-unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo- and enantioselectivities of the isoxazolidines.
引用
收藏
页码:3532 / 3538
页数:7
相关论文
共 67 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]  
[Anonymous], 2010, Angew. Chem., DOI DOI 10.1002/ANGE.200905684
[3]  
[Anonymous], 2004, Angew. Chem, V116, P5248, DOI DOI 10.1002/ANGE.200400650
[4]   Enantioselective organocatalytic indole alkylations. Design of a new and highly effective chiral amine for iminium catalysis [J].
Austin, JF ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (07) :1172-1173
[5]   Enantioselective organocatalysis using SOMO activation [J].
Beeson, Teresa D. ;
Mastracchio, Anthony ;
Hong, Jun-Bae ;
Ashton, Kate ;
MacMillan, David W. C. .
SCIENCE, 2007, 316 (5824) :582-585
[6]   Polymer-supported organic catalysts [J].
Benaglia, M ;
Puglisi, A ;
Cozzi, F .
CHEMICAL REVIEWS, 2003, 103 (09) :3401-3429
[7]  
Benaglia M, 2002, ADV SYNTH CATAL, V344, P149, DOI 10.1002/1615-4169(200202)344:2<149::AID-ADSC149>3.0.CO
[8]  
2-U
[9]   Organocatalysis-after the gold rush [J].
Bertelsen, Soren ;
Jorgensen, Karl Anker .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) :2178-2189
[10]   The first enantioselective organocatalytic Mukaiyama- Michael reaction:: A direct method for the synthesis of enantioenriched γ-butenolide architecture [J].
Brown, SP ;
Goodwin, NC ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (05) :1192-1194