On the Roles of Protic Solvents in Imidazolidinone-Catalyzed Transformations

被引：22

作者：

Brazier, John B. ^{[1
]}

Jones, Kevin M. ^{[1
]}

Platts, James A. ^{[1
]}

Tomkinson, Nicholas C. O. ^{[1
]}

机构：

[1] Cardiff Univ, Sch Chem, Main Bldg,Pk Pl, Cardiff CF10 3AT, S Glam, Wales

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 07期

基金：

英国工程与自然科学研究理事会;

关键词：

Diels-Alder reaction; imidazolidinone; iminium ion catalysis; organocatalysis; IMINIUM ION CATALYSIS; DIELS-ALDER REACTION; ORGANIC CATALYSIS; X-RAY; ORGANOCATALYSIS; STRATEGIES; CYCLOADDITION; CYCLIZATION; ADVENT; PHASE;

D O I：

10.1002/anie.201005892

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Step by step: The effect of protic solvents on the rate and stereochemical outcome of the imidazolidinone-catalyzed Diels-Alder cycloaddition was rationalized. The following picture emerges: the solvent accelerates iminium ion formation (stepa 1), the Diels-Alder cycloaddition is reversible (stepa 2), and the solvent intercepts the iminium ion adduct (stepa 3). © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1613 / 1616

页数：4

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