Highly active asymmetric Diels-Alder reactions catalyzed by C2-symmetric bipyrrolidines: catalyst recycling in water medium and insight into the catalytic mode

被引：18

作者：

Ma, Yuanhui ^{[1
]}

Jin, Shangbin ^{[1
]}

Kan, Yuhe ^{[2
]}

Zhang, Yong Jian ^{[1
]}

Zhang, Wanbin ^{[1
]}

机构：

[1] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

[2] Huaiyin Normal Univ, Sch Chem & Chem Engn, Huaian 223300, Jiangshu, Peoples R China

来源：

TETRAHEDRON | 2010年 / 66卷 / 21期

基金：

中国国家自然科学基金;

关键词：

DIARYLPROLINOL SILYL ETHER; CLAISEN REARRANGEMENT; ALDOL REACTIONS; DIAMINE SALTS; ORGANOCATALYSTS; SULFONAMIDE; ALDEHYDES; DIENES; BOND;

D O I：

10.1016/j.tet.2010.03.042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new class of C-2-symmetric 3,3'-dialkoxy-2,2'-bipyrrolidines have been designed and synthesized for asymmetric organocatalytic Diels-Alder reactions of alpha,beta-unsaturated aldehydes. The remarkable rate-accelerating effect for the cycloaddition reaction has been observed in aqueous medium. The catalyst 1c center dot 2HClO(4) can be recovered and reused several times by simple extraction without significant loss of catalytic activity and stereoselectivity. The catalytic mode has been demonstrated by DFT calculation, NMR, and X-ray crystallographic studies for diiminium intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：3849 / 3854

页数：6

共 15 条

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Ma, Yuanhui
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Lee, Junseong
Zhang, Wanbin
TETRAHEDRON LETTERS, 2009, 50 (52) : 7388 - 7391
[2] C2-symmetric bissulfoximines as ligands in copper-catalyzed enantioselective Diels-Alder reactions
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ORGANIC LETTERS, 2003, 5 (04) : 427 - 429
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Manickam, G
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TETRAHEDRON-ASYMMETRY, 1999, 10 (15) : 2913 - 2925
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Tetrahedron Lett, 11 (1725):
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[9] Synthesis and diastereoselective Diels-Alder reactions of homochiral C2-symmetric butane-1,2-diacetal-based 1,3-dienes
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