Functionalized ionic liquids catalyzed direct aldol reactions

被引：143
|
作者：
Luo, Sanzhong [1 ]
Mi, Xueling
Zhang, Long
Liu, Song
Xu, Hui
Cheng, Jin-Pei
机构：
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, Beijing 100080, Peoples R China
[2] Nankai Univ, Dept Chem, Tianjin 300071, Peoples R China
[3] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
来源：
TETRAHEDRON | 2007年 / 63卷 / 09期
基金：
中国国家自然科学基金;
关键词：
functionalized ionic liquids; organocatalyst; direct aldol reaction;
D O I：
10.1016/j.tet.2006.12.079
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A series of functionalized ionic liquids (FILs) incorporated with chiral-pyrrolidine unit have been synthesized and tested as reusable organocatalysts for direct aldol reactions. FIL 1b in combination with acetic acid and water as additives could effectively catalyze direct aldol reactions of various ketone donors in high yields and the FIL catalyst was easily recycled and reused for six times with slight reduction in activity. Based on experimental observations as well as previous reports, we proposed that the reactions occurred via syn-enamine intermediate and the ionic-liquid moiety in the FIL provides some space shielding for the participating aldehyde acceptors that accounts for the modest enantioselectivities observed in the reactions. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1923 / 1930
页数：8
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