1,2-Dihydropentalenes from Fulvenes by [6 + 2] Cycloadditions with 1-Isopropenylpyrrolidine

• Published in: Organic letters Vol. 13; no. 22; pp. 5952 - 5955
• Main Authors: Coşkun, Necdet, Ma, Jingxiang, Azimi, Saeed, Gärtner, Christian, Erden, Ihsan
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 18.11.2011; Amer Chemical Soc
• Subjects: Catalysis; Chemistry; Chemistry, Organic; Cyclopentanes - chemical synthesis; Cyclopentanes - chemistry; Hydrogenation; Molecular Structure; Physical Sciences; Pyrrolidines - chemistry; Science & Technology; SUBSTITUTED FULVENES; CHEMISTRY; ACETONE; ROUTE; SINGLET OXYGEN; ALLENE OXIDE

In situ generated acetone pyrrolidine enamine undergoes [6 + 2] cycloadditions with fulvenes to give 1,2-dihydropentalenes. This ring annulation method works particularly well with 6-monosubstituted fulvenes and is subject to steric hindrance at C-6 of the fulvene. On the basis of mechanistic studie...