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

• Published in: Organic letters Vol. 19; no. 17; pp. 4616 - 4619
• Main Authors: Shen, Yangyong, Huang, Bo, Zeng, Linwei, Cui, Sunliang
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.09.2017; Amer Chemical Soc
• Subjects: aldehydes; amides; carboxylic acids; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; phthalides; Physical Sciences; Science & Technology; synthesis; ASYMMETRIC MULTICOMPONENT REACTIONS; ALKENES; YNAMIDES; ACID; ISOCYANIDES; UGI 4-COMPONENT CONDENSATION; EFFICIENT SYNTHESIS; CHEMISTRY; BOND FORMATION; DIVERSITY
• ISSN: 1523-7060; 1523-7052; 1523-7052
• DOI: 10.1021/acs.orglett.7b02232

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.