Seebach's oxazolidinone is a good catalyst for aldol reactions

被引：44

作者：

Isart, Caries ^{[1
]}

Bures, Jordi ^{[1
]}

Vilarrasa, Jaume ^{[1
]}

机构：

[1] Univ Barcelona, Fac Quim, Dept Quim Organ, Barcelona 08028, Spain

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 37期

关键词：

organocatalysis; proline; bicyclic oxazolidinones; aldol reactions;

D O I：

10.1016/j.tetlet.2008.07.028

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Seebach's proline-derived oxazolidinone 2d overcomes (S)-proline and is at least as efficient as (S)-5(pyrrolidin-2-yl)tetrazole in several organocatalytic aldol reactions examined. A quick exchange takes place between 2d and carbonyl Compounds that gives new bicyclic oxazolidinones, in equilibrium with the very minor active species (enamines). Maximum yields of the aldols (beta-hydroxy ketones) were achieved after 1-4 h when, with proline, they are attained after 30-48 h. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5414 / 5418

页数：5

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