engleski

Passerini reaction of carbohydrate derivatives

Carbohydrates represent the most abundant class of natural products with distinctive role in different biological processes and they are highly valuable pool of chiral molecular scaffolds [1]. Multicomponent reactions (MCRs) offer an attractive one-pot strategy for generating a library of highly functionalized and complex organic compounds in modern synthetic chemistry. Utilization of carbohydrates and their derivatives in MCRs is based on their polyfunctional character and stereochemical diversity [2, 3]. The Passerini reaction is an isonitrile-based MCR that yields α- acyloxy carboxamides from an aldehyde, an isonitrile, and a carboxylic acid. Our initial efforts were directed toward exploitation of 2- isocyanoglucosyl derivative in the Passerini reaction with various aldehydes and carboxylic acids. Next, we used for the first time a highly strained D-fructose-derived aldehyde in the Passerini reaction with commercially available and sugar-derived isocyanides and notices a highly diastereoselective character of this reaction.

Multicomponent reactions ; Passerini reaction ; carbohydrate ; aldehydes

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