As one of the most important building blocks in organic synthesis, isocyanides
come in for a wide range of transformations owing mostly to their unusual terminal carbon
center adsorbed electrophiles, reacted with nucleophiles, get involved in radical reactions
and coordinated with metal centers. The distinctive feature of isocyanide is its ready willingness
to participate in multicomponent reactions (MCRs). MCRs represent a great tool
in organic synthesis for the construction of new lead structures in a single procedure
introducing both structural diversity and molecular complexity in only one step.
Isocyanide-based multicomponent reactions (IMCRs) have become a powerful approach
for the synthesis of complex molecules providing high degree of atom and bond economy
under very mild reaction conditions. The use of enantiomerically pure isocyanides can, in
principle, bring about two advantages: (i) the possibility to obtain a stereochemically diverse adduct, controlling
the absolute configuration of the starting isocyanide; and (ii) the possibility to induce diastereoselection in
the multicomponent reaction. The most commonly-used IMCRs are the Ugi and Passerini reactions. Many
published reviews have focused on the Ugi and Passerini reactions from different viewpoints, but this review
describes advances in the application of chiral isocyanides in MCRs. The rationale for applying such diversity
generating chemistries is also discussed.
Keywords: Chiral compounds, Isocyanide, Multicomponent reactions, Passerini reaction, Ugi reaction, Asymmetric synthesis.
Rights & PermissionsPrintExport