N-Arylprolinamide as an organocatalyst for the direct asymmetric aldol reaction of acetone with isatin

被引：22

作者：

Yadav, Geeta Devi ^{[1
]}

Singh, Surendra ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Delhi 110007, India

来源：

TETRAHEDRON-ASYMMETRY | 2016年 / 27卷 / 2-3期

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; SOLVENT-FREE CONDITIONS; STEREOSELECTIVE-SYNTHESIS; UNACTIVATED KETONES; PROLINE; ACETALDEHYDE; CATALYST; 3-ALKYL-3-HYDROXYINDOLIN-2-ONES; CONVOLUTAMYDINE; DERIVATIVES;

D O I：

10.1016/j.tetasy.2015.12.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

N-Aryl-(S)-prolinamides act as organocatalysts for the direct asymmetric aldol reaction between isatin and acetone. N-(4-Bromophenyl)-(S)-prolinamide (20 mol %) efficiently catalysed the direct aldol reaction between isatin and acetone at -35 degrees C, and afforded 3-alkyl-3-hydroxyindolin-2-one in 99% yield and with 71% ee. We have generalised the methodology for the direct asymmetric aldol reaction between isatin derivatives and acetone, and the corresponding aldol products were obtained in 76-99% yields and with 42-87% ee. (C) 2015 Elsevier Ltd. All rights reserved.

引用

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页码：123 / 129

页数：7

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