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

Coskun N., Ma J., Azimi S., Gaertner C., Erden I.

ORGANIC LETTERS, cilt.13, sa.22, ss.5952-5955, 2011 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 13 Sayı: 22
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1021/ol202222d
  • Dergi Adı: ORGANIC LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.5952-5955
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

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 studies, optimal conditions have been developed for a one-pot synthesis of 1,2-dihydropentalenes using catalytic amounts of pyrrolidine.