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

• Published in: Tetrahedron letters Vol. 53; no. 40; pp. 5360 - 5363
• Main Authors: Neves Filho, Ricardo A.W., Stark, Sebastian, Morejon, Micjel C., Westermann, Bernhard, Wessjohann, Ludger A.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 03.10.2012; Elsevier
• Subjects: Activated amides; Activated carboxylic acids; Amides; Carboxylic acids; Chemistry; Chemistry, Organic; Equivalence; Esters; Formate carbanion equivalent; Functional group interconversions; Isocyanides; N-Acylpyrroles; Nucleophiles; Olefins; Passerini reaction; Physical Sciences; Science & Technology; Synthesis; Tetrahedrons; Ugi reaction; Ugi-Smiles reaction; Activated amides; Ugi reaction; Formate carbanion equivalent; Functional group interconversions; N-Acylpyrroles; Activated carboxylic acids; Passerini reaction; Isocyanides; Ugi-Smiles reaction; ANALOGS; CONVERSION; UGI 4-COMPONENT CONDENSATION; VERSATILE; DIVERSITY
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2012.07.064

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−).