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

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.