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Lewis acid-catalyzed formation of Ugi four-component reaction product from Passerini three-component reaction system without an added amine |
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| Authors: | Wei-Min Dai Huoming Li |
| Institution: | aLaboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, China bDepartment of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China |
| Abstract: | In the presence of a Lewis acid the phenol-Passerini three-component reaction (phenol-P-3CR) system is found to deliver a product of the phenol-Ugi four-component reaction (phenol-U-4CR). It is the first demonstration of an isocyanide as an amine equivalent in isocyanide-based multicomponent reactions (IMCRs). In general, by using Ti(O-i-Pr)4 in MeOH both phenol-U-4CR and U-4CR products are synthesized from an aromatic aldehyde, a phenolic or carboxylic acid, and an isocyanide. Moreover, by using MeCN as the solvent, the phenol-P-3CR products can be obtained in good yields without contamination of the phenol-U-4CR products. |
| Keywords: | Lewis acid Phenols P-3CR Smiles rearrangement U-4CR |
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