title: Divergent dendrimer synthesis via the Passerini three-component reaction and olefin cross-metathesis.
abstract: The combination of the Passerini reaction and olefin cross-metathesis is shown to be a very useful approach for the divergent synthesis of dendrimers. Castor oil-derived platform chemicals, such as 10-undecenoic acid and 10-undecenal, are reacted in a Passerini reaction with an unsaturated isocyanide to obtain a core unit having three terminal double bonds. Subsequent olefin cross-metathesis with tert-butyl acrylate, followed by hydrogenation of the double bonds and hydrolysis of the tert-butyl ester, leads to an active core unit bearing three carboxylic acid groups as reactive sites. Iterative steps of the Passerini reaction with 10-undecenal and 10-isocyanodec-1-ene for branching, and olefin cross-metathesis with tert-butyl acrylate, followed by hydrogenation and hydrolysis allow the synthesis of a third-generation dendrimer. All steps of the synthesis are carefully characterized by NMR, GPC, MS, and IR.
authors.forename: Oliver
authors.initials: O
authors.lastname: Kreye
authors.forename: Dennis
authors.initials: D
authors.lastname: Kugele
authors.forename: Lorenz
authors.initials: L
authors.lastname: Faust
authors.forename: Michael A R
authors.initials: MA
authors.lastname: Meier
mesh_terms: D000179:Acrylates / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D050091:Dendrimers / Q000138:chemical synthesis*; D006865:Hydrogenation
chemical_list: D000179:Acrylates; D000475:Alkenes; D050091:Dendrimers; C522411:tert-butyl acrylate