ChemInform Abstract: Palladium(0)-Catalyzed Domino Cyclization—Carbonylation of Alkenyl-Allenyl-Allylic Acetate.

✍ Scribed by Takayuki Doi; Masaru Takasaki; Sadahiro Nakanishi; Arata Yanagisawa; Keiji Yamamoto; Takashi Takahashi

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 34 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199913104

✦ Synopsis

Palladium(0)-Catalyzed Domino Cyclization-Carbonylation of Alkenyl-Allenyl-Allylic Acetate. -Optimum reaction conditions for the domino cyclization-carbonylation of title acetate (I) are presented, involving five and six consecutive C-C bond forming steps. Palladium-catalyzed reaction of title acetate (I) in acetic acid under carbon monoxide at 70 • C affords the monocyclopentene derivative (II) as a primary product, which undergoes further cyclization-carbonylation under decreased CO pressure to furnish a mixture of tri-(VII) and tetrakiscyclopentane (VI) and acetate (V). At 90 • C, the formation of acetate can be suppressed, furnishing target compounds (VI) and (VII) in 77% combined yield. -(DOI, TAKAYUKI; TAKASAKI, MASARU;