Organocatalyzed enantioselective aldol reaction of 1H-pyrrole-2,3-diones

被引：10

作者：

Bhanushali, Mayur ^{[1
]}

Zhao, Cong-Gui ^{[1
]}

机构：

[1] Univ Texas San Antonio, Dept Chem, San Antonio, TX 78249 USA

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 03期

关键词：

Aldol reaction; 1H-Pyrrole-2,3-dione; 3-Hydroxy-1H-pyrrol-2(3H)-one; Organocatalysis; Enantioselective; Proline; Cinchona alkaloid; CATALYTIC ASYMMETRIC EPOXIDATION; ALPHA; BETA-UNSATURATED KETONES; PROLINE DERIVATIVES; ENAMINE CATALYSIS; MICHAEL ADDITION; ALPHA-HYDROXYPHOSPHONATES; UNACTIVATED KETONES; WATER; MOLECULES; EFFICIENT;

D O I：

10.1016/j.tetlet.2011.11.056

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantioselective cross aldol reaction of 1-benzyl 4,5-dioxo-2-aryl-4,5-dihydro-1H-pyrrole-3-carboxylates and ketones was studied with praline derivatives or cinchona alkaloid-derived primary amines as the catalysts for the first time. trans-4-Benzoyloxy-L-proline (15) was found to be the best catalyst for acyclic ketones. For cyclohexanone, the best results were achieved with 9-deoxy-9-epi-aminoquinine (18) as the catalyst in the presence of racemic 1,1'-binaphthyl-2,2'-diyl hydrogen phosphate (19) as the cocatalyst. Using these protocols, 3-alkyl-3-hydroxy-1H-pyrrol-2(3H)-one derivatives were obtained in excellent yields and good to high ee values (up to 94% ee). (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：359 / 362

页数：4

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