Gold(I)-catalyzed domino reaction of allyl 2-en-4-ynyl ethers to 1,3,6-trien-4-yl ketones

• Verfasst von: Hashmi, A. Stephen K. [VerfasserIn]
• Verfasst von: Graf, Katharina [VerfasserIn]
• Verfasst von: Ackermann, Martin [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Titel: Gold(I)-catalyzed domino reaction of allyl 2-en-4-ynyl ethers to 1,3,6-trien-4-yl ketones
• Verf.angabe: A. Stephen K. Hashmi, Katharina Graf, Martin Ackermann, and Frank Rominger
• E-Jahr: 2013
• Jahr: March 7, 2013
• Umfang: 5 S.
• Teil: volume:5
• Teil: year:2013
• Teil: number:5
• Teil: pages:1200-1204
• Teil: extent:5
• Fussnoten: Gesehen am 08.10.2021
• Titel Quelle: Enthalten in: ChemCatChem
• Ort Quelle: Weinheim : WILEY-VCH Verlag, 2009
• Jahr Quelle: 2013
• Band/Heft Quelle: 5(2013), 5, Seite 1200-1204
• ISSN Quelle: 1867-3899
• DOI: doi:10.1002/cctc.201200787
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: alkenes
• Sach-SW: alkynes
• Sach-SW: ethers
• Sach-SW: gold
• Sach-SW: ketones
• K10plus-PPN: 1749496437

Abstract

The gold(I)-catalyzed reaction of allyl 2-en-4-ynyl ethers provides stereoselectively (Z)-1,3,6-trienes with an acyl substitutent in the 4-position. The reaction proceeds through an oxygen transfer along the chain and a clean allylic inversion. This complements the preceding work by Gagosz, who obtained furan derivatives in his investigation of similar substrates with terminal alkynyl groups.10, 16 The only drawback of this mechanistically new pathway is the instability of the products under the reaction conditions, which sometimes prevents their isolation in high yields.