Research Article

Asymmetric phosphoric acid–catalyzed four-component Ugi reaction

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Science  14 Sep 2018:
Vol. 361, Issue 6407, eaas8707
DOI: 10.1126/science.aas8707

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Steering together all four Ugi pieces

The nearly 60-year-old Ugi reaction is a remarkably efficient means of linking together four molecular building blocks: an aldehyde, an amine, a carboxylic acid, and an isocyanide. Because each component is independently tunable, the reaction is especially well suited to the assembly of diverse compound libraries. However, stereoselectivity has been a challenge. Zhang et al. now show that chiral phosphoric acids can catalyze the four-component coupling with high enantioselectivity (see the Perspective by Riva). Theory suggests that a hydrogen-bonded complex involving the phosphoric acid and carboxylic acid sets the stereochemistry for isocyanide attack on an imine intermediate.

Science, this issue p. eaas8707; see also p. 1072