Ngouansavanh, TifelleZhu, Jieping2010-11-252010-11-252010-11-25200610.1002/anie.200600588https://infoscience.epfl.ch/handle/20.500.14299/58442An alc. instead of an aldehyde was found to be an effective reaction partner in the three-component Passerini reaction (P-3CR) in the presence of o-iodoxybenzoic acid (IBX). Thus, by simply heating a soln. of an alc. R1CH2OH [R1 = n-Pr, Ph, PhCH2, AcO(CH2)5, PhCH2OCONHCH2, (R)-AcNHCH(CH2Ph), etc.], a carboxylic acid R2CO2H [R2 = Me, Ph, (S)-MeOCHPh, etc.], an isonitrile R3NC (R3 = Me3C, MeO2CCH2, cyclohexyl, PhCH2), and IBX at 40 DegC, an oxidn./P-3CR sequence occurred smoothly to afford the corresponding alpha -acyloxy carboxamides R2CO2CHR1CONHR3 in good to excellent yields. [on SciFinder (R)]Addition reaction (Passerini; prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); Amides Role: SPN (Synthetic preparation)PREP (Preparation) (acyloxy; prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); Condensation reaction (oxidative; prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); Carboxylic acids; Isocyanides Role: RCT (Reactant)RACT (Reactant or reagent) (prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); Alcohols Role: RCT (Reactant)RACT (Reactant or reagent) (primary; prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid); Coupling reaction (three-component; prepn. of alpha -acyloxy amides by three-component Passerini reaction of alcs. with isonitriles and carboxylic acids in the presence of iodoxybenzoic acid)isonitrile oxidative multicomponent Passerini alc carboxylic iodoxybenzoic acid; amide acyloxy prepntext::journal::journal article::research article