Six- versus five-membered ring formation in radical cyclizations of 7-bromo-substituted hexahydroindolinones

Rashatasakhon P., Ozdemir A., WILLIS J., PADWA A.

ORGANIC LETTERS, vol.6, no.6, pp.917-920, 2004 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 6 Issue: 6
  • Publication Date: 2004
  • Doi Number: 10.1021/ol036347z
  • Journal Name: ORGANIC LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.917-920
  • Istanbul Technical University Affiliated: No


Radical cyclization of N-allyl-7-bromo-3a-methyl-hexahydroindol-2-one affords a six-membered ring product that prevails over the isomeric five-membered compound. The former product is generated through two reaction pathways: (a) 6-endo-trig ring closure and (b) rearrangement of an intermediate methylenecyclopentyl radical obtained by 5-exo-trig cyclization.