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
收藏
页码：5414 / 5418
页数：5
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