Highly efficient direct a larger-scale aldol reactions catalyzed by a flexible prolinamide based-metal Lewis acid bifunctional catalyst in the presence of water

被引：23

作者：

Chen, Guodong ^{[1
]}

Fu, Xiangkai ^{[1
]}

Li, Chao ^{[1
]}

Wu, Chuanlong ^{[1
,2
]}

Miao, Qiang ^{[1
]}

机构：

[1] Southwest Univ, Res Inst Appl Chem, Coll Chem & Chem Engn, Key Lab Appl Chem Chongqing Municipal, Chongqing 400715, Peoples R China

[2] Chongqing Unis Chem Co Ltd, Chongqing 402161, Peoples R China

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2012年 / 702卷

关键词：

Prolinamide base; Metal Lewis acid; Aldol reaction; Aqueous medium; A larger-scale; ORGANIC-REACTIONS; ASYMMETRIC-SYNTHESIS; CYCLIC-KETONES; ALDEHYDES; ORGANOCATALYST; DESIGN; COMPLEX;

D O I：

10.1016/j.jorganchem.2011.12.006

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

In this work, four prolinamide-based organocatalysts were readily synthesized and applied to the asymmetric direct aldol reactions of ketones and aromatic aldehydes in the presence of water. When TFA was used as an acidic additive, 10 mol % loading of 1c afforded aldol products with good diastereoselectivity of up to 91/9 and enantioselectivity of up to 85%. When ZnCl2 was added as a metal Lewis acid additive, the aldol product could be obtained with up to 99/1 dr and 96% ee. This novel prolinamide based-metal Lewis acid bifunctional organocatalyst 1c can be efficiently used in a larger-scale reactions with the enantioselectivities being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier B.V. All rights reserved.

引用

页码：19 / 26

页数：8

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