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1.2.3.1 Third Component Carboxylic Acid (Passerini Reaction)

DOI: 10.1055/sos-SD-210-00184

Riva, R.; Banfi, L.; Basso, A.Science of Synthesis: Multicomponent Reactions, (20141327.

General Introduction

The multicomponent reaction of a carbonyl compound, an isocyanide, and a carboxylic acid to give α-acyloxy amides was discovered in 1921 in Florence (Italy) by Mario Passerini[‌1‌] and as such it is the oldest isocyanide-based multicomponent reaction. For many years, this reaction attracted very little interest until, at the end of the last century, the great usefulness of isocyanide-based multicomponent reactions in combinatorial synthesis was eventually recognized. The classical Passerini reaction allows the synthesis of α-acyloxy amides, including depsipeptides, with the simultaneous introduction of three diversity inputs, under mild conditions and with a high degree of atom economy. However, the scope of this old reaction has been recently expanded, bringing about access to many different scaffolds (including heterocyclic) by using alternatives to carboxylic acids, through intramolecular modifications, or by exploiting post-condensation transformations. The Passerini reaction, or its “truncated” variant, is one of the easiest ways to convert carbonyl compounds into α-acyloxy or α-hydroxy amides, realizing a typical “umpolung” process, with the isocyanide acting as an acyl anion equivalent.

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References