Sequential gold-catalyzed carbene transfer/ring closure

• Verfasst von: Rode, Navnath [VerfasserIn]
• Verfasst von: Adak, Tapas [VerfasserIn]
• Verfasst von: Rudolph, Matthias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Titel: Sequential gold-catalyzed carbene transfer/ring closure
• Titelzusatz: oxidative cyclization of β-(2-Alkynylphenyl)-α,β-ynones to indenofuranones
• Verf.angabe: Navnath Rode, Fabio Marinelli, Antonio Arcadi, Tapas Adak, Matthias Rudolph, Frank Rominger, and A. Stephen K. Hashmi
• Umfang: 5 S.
• Fussnoten: Gesehen am 05.02.2019
• Titel Quelle: Enthalten in: Advanced synthesis & catalysis
• Jahr Quelle: 2018
• Band/Heft Quelle: 360(2018), 24, S. 4790-4794
• ISSN Quelle: 1615-4169
• DOI: doi:10.1002/adsc.201801082
• Datenträger: Online-Ressource
• Sprache: eng
• K10plus-PPN: 1587277492

Abstract

β-(2-Alkynylphenyl)-α,β-ynones undergo a gold-catalyzed oxidative two-fold cyclization in the presence of N-oxides to give 1,3-disubstituted-8H-indeno[1,2-c]furan-8-ones in good yields. This cascade process is triggered by a selective oxygen transfer from an N-oxide onto the gold-activated alkynone to generate a α-dioxocarbene intermediate which, via carbene transfer across the remaining alkyne moiety and subsequent cyclization through nucleophilic attack by a carbonyl oxygen, achieves the construction of 1,3-disubstituted fused polycyclic furans.