Gold catalysis: 1,3-oxazines by cyclisation of allene amides

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Schuster, Andreas M. [VerfasserIn]
• Verfasst von: Litters, Sebastian [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Pernpointner, Markus [VerfasserIn]
• Titel: Gold catalysis: 1,3-oxazines by cyclisation of allene amides
• Verf.angabe: A. Stephen K. Hashmi, Andreas M. Schuster, Sebastian Litters, Frank Rominger, and Markus Pernpointner
• E-Jahr: 2011
• Jahr: 12 April 2011
• Umfang: 7 S.
• Illustrationen: Diagramme
• Fussnoten: Gesehen am 07.09.2022
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2011
• Band/Heft Quelle: 17(2011), 20, Seite 5661-5667
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.201100132
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Druck-Ausgabe: Gold catalysis: 1,3-oxazines by cyclisation of allene amides. - 2011
• Sach-SW: allenes
• Sach-SW: gold
• Sach-SW: heterocycles
• Sach-SW: intermediates
• Sach-SW: labeling studies
• Sach-SW: oxazines
• K10plus-PPN: 1815991143

Abstract

A series of allene amides was prepared and their gold-catalysed cyclisation was investigated. The formation of six-membered rings, 1,3-oxazines, was observed. Dihydropyrroles originating from intramolecular hydroamination of the distal CC double bonds of the allenes were minor side products. Mechanistic studies by in situ 31P NMR spectroscopy showed only one additional species during the conversion in each case; a computational study of the different allyl gold(I) species involved allowed this to be assigned as the σ-allyl gold species bearing the gold catalyst at the sterically less hindered methylene end. The regiospecific deuterodeauration of this intermediate confirmed a SE′-type mechanism for this last step of the catalytic cycle.