4-Isocyanopermethylbutane-1,1,3-triol (IPB): a convertible isonitrile for multicomponent reactions |
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| Authors: | Ricardo A.W. Neves FilhoSebastian Stark Micjel C. MorejonBernhard Westermann Ludger A. Wessjohann |
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| Affiliation: | a Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle (Saale), Germany
b Martin-Luther-University Halle-Wittenberg, Institute of Chemistry, Kurt-Mothes-Str. 2, 06120 Halle (Saale), Germany |
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| Abstract: | 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−). |
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| Keywords: | Functional group interconversions N-Acylpyrroles Activated carboxylic acids Activated amides Ugi reaction Ugi-Smiles reaction Passerini reaction Formate carbanion equivalent Isocyanides |
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