PerspectiveOrganic Chemistry

Enantioselective four-component Ugi reactions

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Science  14 Sep 2018:
Vol. 361, Issue 6407, pp. 1072-1073
DOI: 10.1126/science.aau7497

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In 1921, Passerini (1) reported the reaction that combines an isocyanide with a carbonyl compound (usually an aldehyde) and a carboxylic acid to give a depsipeptide (see the figure). This reaction was the first reported example of a multicomponent reaction (MCR)—one where the product contains essential parts of all of the reactants with the simultaneous generation of several new bonds—based on isocyanides. Such reactions based on isocyanides are called IMCRs. For several years, this reaction received only scant attention; the bad smell of the low–molecular weight isocyanides likely discouraged chemists from exploiting their reactivity. In 1959, the Ugi reaction was reported, in which a fourth component—a primary amine—allows for the formation of a peptide-like structure with the introduction of a new stereogenic center (2). On page 1087 of this issue, Zhang et al. (3) now report an enantioselective organocatalytic four-component Ugi reaction.