A Reaction of Triazoles with Thioesters to Produce [beta]-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond

A Reaction of Triazoles with Thioesters to Produce [beta]-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond

N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce [beta]-sulfanyl enamides in a stereoselective manner. The reaction proceeds through generation of an [alpha]-imino rhodium carbene complex, nucleophilic addition of the sulfur atom of a thioester on...

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Bibliographic Details
Published in:Angewandte Chemie Vol. 127; no. 34; p. 10105
Main Authors: Miura, Tomoya, Fujimoto, Yoshikazu, Funakoshi, Yuuta, Murakami, Masahiro
Format: Journal Article
Language:German
Published: Weinheim Wiley Subscription Services, Inc 17-08-2015
Subjects:
Chemistry
Sulfur
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Summary:N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce [beta]-sulfanyl enamides in a stereoselective manner. The reaction proceeds through generation of an [alpha]-imino rhodium carbene complex, nucleophilic addition of the sulfur atom of a thioester onto the carbenoid carbon atom, and subsequent intramolecular migration of the acyl group from the sulfur atom to the imino nitrogen atom. The method is successfully applied to a ring-expansion reaction of thiolactones, thus leading to the formation of sulfur-containing lactams.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201504013