Organic Letters
Organic Letters
5 years ago

Single Reactant Replacement Approach of Passerini Reaction: One-Pot Synthesis of β-Acyloxyamides and Phthalides

Single Reactant Replacement Approach of Passerini Reaction: One-Pot Synthesis of β-Acyloxyamides and Phthalides
Sunliang Cui, Bo Huang, Linwei Zeng, Yangyong Shen
The Passerini reaction is a classical and well-known multicomponent reaction for accessing α-acyloxy amides. A single reactant replacement (SRR) approach of Passerini reaction is described, which involves aldehydes, carboxylic acids, and ynamides to constitute a one-pot synthesis of β-acyloxy amides in a convergent manner. When this method was subject to intramolecular reaction, the process would produce phthalide products. The scalability was demonstrated, and a crossover reaction was conducted to elucidate a plausible mechanism.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02232

DOI: 10.1021/acs.orglett.7b02232

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