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

被引：45
作者：
Haraguchi, Naoki [1 ]
Takemura, Yu [1 ]
Itsuno, Shinichi [1 ]
机构：
[1] Toyohashi Univ Technol, Dept Mat Sci, Toyohashi, Aichi 4418580, Japan
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 08期
关键词：
ORGANIC CATALYSIS; STRATEGIES; ALKYLATIONS; ADVENT; ALDOL; AMINE;
D O I：
10.1016/j.tetlet.2009.12.088
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The polymer-supported organocatalyst was prepared by ion exchange reaction of MacMillan iminium catalyst with polymer-supported sulfonic acids. Resulting polymeric organocatalyst was effective for Diels-Alder reaction of 1,3-cyclopentadiene and trans-cinnamaldehyde in CH3OH/H2O, affording good enantioselectivity and reusability. (C) 2009 Elsevier Ltd. All rights reserved.
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收藏
页码：1205 / 1208
页数：4
相关论文
共 31 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]   An Immobilization Method of Chiral Quaternary Ammonium Salts onto Polymer Supports [J].
Arakawa, Yukihiro ;
Haraguchi, Naoki ;
Itsuno, Shinichi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (43) :8232-8235
[3]   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
[4]   Polymer-supported organic catalysts [J].
Benaglia, M ;
Puglisi, A ;
Cozzi, F .
CHEMICAL REVIEWS, 2003, 103 (09) :3401-3429
[5]  
Benaglia M, 2002, ADV SYNTH CATAL, V344, P149, DOI 10.1002/1615-4169(200202)344:2<149::AID-ADSC149>3.0.CO
[6]  
2-U
[7]   QUANTITATIVE ANTIHYDROPHOBIC EFFECTS AS PROBES FOR TRANSITION-STATE STRUCTURES .2. DIELS-ALDER REACTIONS [J].
BRESLOW, R ;
ZHU, ZN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9923-9924
[8]   CHAOTROPIC SALT EFFECTS IN A HYDROPHOBICALLY ACCELERATED DIELS-ALDER REACTION [J].
BRESLOW, R ;
RIZZO, CJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4340-4341
[9]   The hydrophobic effect as a mechanistic tool [J].
Breslow, R ;
Groves, K ;
Mayer, MU .
PURE AND APPLIED CHEMISTRY, 1998, 70 (10) :1933-1938
[10]   Direct and enantioselective organocatalytic α-chlorination of aldehydes [J].
Brochu, MP ;
Brown, SP ;
MacMillan, DWC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4108-4109
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