4-Isocyanopermethylbutane-1,1,3-triol (IPB): a convertible isonitrile for multicomponent reactions

被引：29

作者：

Neves Filho, Ricardo A. W. ^{[1
]}

Stark, Sebastian ^{[1
]}

Morejon, Micjel C. ^{[1
]}

Westermann, Bernhard ^{[1
,2
]}

Wessjohann, Ludger A. ^{[1
,2
]}

机构：

[1] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale, Germany

[2] Univ Halle Wittenberg, Inst Chem, D-06120 Halle, Saale, Germany

来源：

TETRAHEDRON LETTERS | 2012年 / 53卷 / 40期

关键词：

Functional group interconversions; N-Acylpyrroles; Activated carboxylic acids; Activated amides; Ugi reaction; Ugi-Smiles reaction; Passerini reaction; Formate carbanion equivalent; Isocyanides; UGI 4-COMPONENT CONDENSATION; N-ACYLPYRROLES; DIVERSITY; VERSATILE; ANALOGS; ISOCYANIDES; CONVERSION;

D O I：

10.1016/j.tetlet.2012.07.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and applications of 4-isocyanopermethylbutane-1,1,3-triol (IPB) as a new convertible isonitrile (isocyanide) for isocyanide-based multicomponent reactions (IMCRs) like Ugi, Ugi-Smiles, and Passerini reactions are described. The primary products obtained from these IMCRs can be converted into highly activated N-acylpyrroles, which upon treatment with nucleophiles can be transformed into carboxylic acids, esters, amides, alcohols, and olefins. In this sense the reagent can be seen as a neutral carbanion equivalent to formate (HO2C-), and carboxylates or carboxamides etc. (RNu-CO-). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：5360 / 5363

页数：4

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