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

页码：1082 / 1088

页数：7

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