4-Acetoxycyclopent-2-enone: a synthetic equivalent for cyclopentadienone in diels-alder reactions

✍ Scribed by P.P.M.A. Dols; L. Lacroix; A.J.H. Klunder; B. Zwanenburg

• Book ID: 104216184
• Publisher: Elsevier Science
• Year: 1991
• Tongue: French
• Weight: 319 KB
• Volume: 32
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)79782-6

✦ Synopsis

The Lewis acid catalyzed Diels-Alder reactions of 4-acetoxycyclopentenone 3 with both cyclic and acyclic dienes is described. Subsequent base induced elimination of the B-acetoxy group from the respective cycloadducts Ieaak to bi-and tricyclic erwnes in good yields. The x-facial diastereoselectivity of the cycloaddition ofS_ with cyclopentadiene is 3:1, in favor of the anti-adduct &J