DTBP‐promoted Passerini‐type reaction of isocyanides with aldehydes: Synthesis of α‐acyloxycarboxamides

• Published in: Journal of the Chinese Chemical Society (Taipei) Vol. 69; no. 10; pp. 1794 - 1802
• Main Authors: Wang, Zhuo, Zhang, Yan, Wu, Zi‐Han, Zhao, Yu‐Long
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley‐VCH Verlag GmbH & Co. KGaA 01.10.2022; Wiley Subscription Services, Inc
• Subjects: aldehyde; Aldehydes; Functional groups; isocyanides; Passerini reaction; α‐acyloxycarboxamides
• ISSN: 0009-4536; 2192-6549
• DOI: 10.1002/jccs.202200290

A novel DTBP‐promoted Passerini‐type reaction of isocyanides with two molecular aldehydes has been developed. This reaction is applicable for a wide range of isocyanides and aldehydes and provides an efficient method for the synthesis of α‐acyloxycarboxamides with two identical functional groups in good to high yields in a single step. The experimental results clearly confirmed the role of water and provided a better mechanistic understanding of this reaction. A novel DTBP‐promoted Passerini‐type reaction of isocyanides with two molecular aldehydes has been developed. This reaction is applicable for a wide range of isocyanides and aldehydes and provides an efficient method for the synthesis of α‐acyloxycarboxamides with two identical functional groups in good to high yields in a single step.