Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 17, Pages 3081-3087Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200544
Keywords
Esters; Oxazoles; Rhodium; Triazoles; Ylides
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Funding
- Japanese Society of Promotion of Sciences (JSPS) [19K05459, 19K16317, 18K06582]
- MEXT Project for promoting public utilization of advanced research infrastructure [JPMXS0422500320]
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A rhodium-catalyzed reaction has been developed to convert N-sulfonyl-1,2,3-triazoles and carboxylic esters into 2,5-disubstituted oxazole derivatives under mild reaction conditions.
A rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with carboxylic esters followed by acid-mediated aromatization has been developed, affording a variety of 2,5-disubstituted oxazole derivatives in good to high yields under mild reaction conditions. The present transformation is proposed to involve the intermolecular carbonyl ylide formation between in situ generated alpha-imino rhodium carbene species and carboxylic esters, which undergoes the nucleophilic attack of the neighboring alpha-imino moiety.
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