Effect of additives on the proline-catalyzed ketone-aldehyde aldol reactions

被引：223

作者：

Pihko, PM ^{[1
]}

Laurikainen, KM ^{[1
]}

Usano, A ^{[1
]}

Nyberg, AI ^{[1
]}

Kaavi, JA ^{[1
]}

机构：

[1] Aalto Univ, Dept Chem Technol, FI-02015 Helsinki, Finland

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

基金：

芬兰科学院;

关键词：

aldehydes; aldol reactions; bases; ketones; organocatalysis; proline; water;

D O I：

10.1016/j.tet.2005.09.070

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The effect of bases, acids, and water as additives in profine-catalyzed ketone-aldehyde aldol reactions has been studied. While the reaction appears to be relatively tolerant to small amounts of tertiary amine bases or weak acids, it stops completely with strong acids. The use of water as an additive had a highly beneficial effect on reactions that were conducted with a stoichiometric ratio of ketone to aldehyde, especially with cyclic ketones. This allows the efficient use of more precious ketones such as 4-thianone as donors in the direct enantioselective aldol and facilitates purification. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：317 / 328

页数：12

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