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...

Full description

Saved in:
Bibliographic Details
Published inAngewandte Chemie Vol. 127; no. 34; p. 10105
Main Authors Miura, Tomoya, Fujimoto, Yoshikazu, Funakoshi, Yuuta, Murakami, Masahiro
Format Journal Article
LanguageGerman
Published Weinheim Wiley Subscription Services, Inc 17.08.2015
Subjects
Chemistry
Sulfur
Online AccessGet full text

Cover

More Information
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