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Synthetic Applications of Passerini Reaction

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Passerini reaction involving an oxo component, an isocyanide, and a nucleophile in a single step to prepare α-acyloxy carboxamide, was first discovered by Passerini about 90 years ago. Various modifications of this reaction have already been developed such as Lewis acids catalysis, in situ oxidation of alcohols to aldehydes, in situ oxidation of aldehydes to carboxylic acids, direct alkylative Passerini reaction, etc. The Passerini reaction has developed in organic synthesis, the total synthesis of natural products, synthesis of polycyclics, macrocycles, heterocycles and pharmaceutical industry for the synthesis of drug-like compounds. The Passerini products could be later cyclized by another type of ring-closing reaction. The aim of this review is to provide an overview of synthetic applications of Passerini reaction.
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Keywords: N-protected amino acid; Passerini reaction; aliphatic; aromatic; carboxylic acid; domino process; heteroaromatic carboxylic ester derivatives; heterocycles; isocyanide; macrocycles; multicomponent reaction; multicomponent reactions (MCRs); α-acyloxy carboxamide; α-acyloxy carboxamide moiety

Document Type: Research Article

Publication date: February 1, 2012

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