Synthesis of planar chiral [2.2]paracyclophane-based amino thioureas and their application in asymmetric aldol reactions of ketones with isatins

被引：23
|
作者：
Lu, Yu [1 ]
Ma, Yudao [1 ]
Yang, Shaobo [1 ]
Ma, Manyuan [1 ]
Chu, Honju [1 ]
Song, Chun [1 ]
机构：
[1] Shandong Univ, Dept Chem, Jinan 250100, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 18期
基金：
中国国家自然科学基金;
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; MICHAEL ADDITION; ALPHA; BETA-UNSATURATED IMIDES; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; BETA-BORATION; CATALYSIS; LIGANDS; ACIDS; ORGANOCATALYSTS;
D O I：
10.1016/j.tetasy.2013.07.023
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Several novel [2.2]paracyclophane-based amino thioureas have been designed and synthesized. The [2.2]paracyclophane-based amino thioureas were used as bifunctional catalysts for organocatalytic enantioselective aldol reactions between ketones and isatins, affording the desired adducts containing a chiral tertiary alcohol in high yields (up to 92% yield) and with good enantioselectivity (up to 88% ee). This is a successful example of employing planar chiral [2.2]paracyclophane-based amino thioureas in asymmetric aldol reactions. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1082 / 1088
页数：7
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