From propargylic amides to functionalized oxazoles

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Blanco Jaimes, Maria Camila [VerfasserIn]
• Verfasst von: Schuster, Andreas M. [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: From propargylic amides to functionalized oxazoles
• Titelzusatz: Domino gold catalysis/oxidation by dioxygen
• Verf.angabe: A. Stephen K. Hashmi, Maria Camila Blanco Jaimes, Andreas M. Schuster, and Frank Rominger
• E-Jahr: 2012
• Jahr: July 17, 2012
• Umfang: 15 S.
• Fussnoten: Gesehen am 06.09.2018
• Titel Quelle: Enthalten in: The journal of organic chemistry
• Ort Quelle: [S.l.] : American Chemical Society, 1936
• Jahr Quelle: 2012
• Band/Heft Quelle: 77(2012), 15, Seite 6394-6408
• ISSN Quelle: 1520-6904
• DOI: doi:10.1021/jo301288w
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: From propargylic amides to functionalized oxazoles. - 2012
• K10plus-PPN: 1580750869

Abstract

A new, highly efficient, and atom-economic access to a series of functionalized 2,5-disubstituted oxazoles from propargylic amides is reported. A series of propargylic amides were transformed to the corresponding alkylideneoxazolines by a gold(I) catalyst. The next step was an autoxidation to hydroperoxides bearing the heteroaromatic oxazoles. Experiments addressing the reaction mechanism reveal a radical pathway for this autoxidation process. The hydroperoxides could conveniently be converted to the corresponding alcohols by reduction with sodium borohydride.