title: A Reaction of Triazoles with Thioesters to Produce β-Sulfanyl Enamides by Insertion of an Enamine Moiety into the Sulfur-Carbonyl Bond.
abstract: N-Sulfonyl-1,2,3-triazoles react with thioesters in the presence of a rhodium(II) catalyst to produce β-sulfanyl enamides in a stereoselective manner. The reaction proceeds through generation of an α-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.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). tmiura@sbchem.kyoto-u.ac.jp.
authors.forename: Tomoya
authors.initials: T
authors.lastname: Miura
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
authors.forename: Yoshikazu
authors.initials: Y
authors.lastname: Fujimoto
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan).
authors.forename: Yuuta
authors.initials: Y
authors.lastname: Funakoshi
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510 (Japan). murakami@sbchem.kyoto-u.ac.jp.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Murakami
keywords: carbenoids; copper; heterocycles; rhodium; sulfur