Journal
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
Volume 69, Issue 10, Pages 1794-1802Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.202200290
Keywords
aldehyde; isocyanides; Passerini reaction; alpha-acyloxycarboxamides
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Funding
- National Natural Science Foundation of China [21871044, 21472017]
- Natural Science Foundation of Jilin Province [20190201073JC]
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A novel DTBP-promoted Passerini-type reaction has been developed for the efficient synthesis of alpha-acyloxycarboxamides with two identical functional groups in a single step. The wide applicability of this reaction to various isocyanides and aldehydes has been demonstrated, and the role of water in the reaction mechanism has been clarified.
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 alpha-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.
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