Cyclization cascade of allenyl azides: A dual mechanism

Carlos Silva López, Olalla Nieto Faza, Ken S. Feldman, Malliga R. Iyer, D. Keith Hester

Research output: Contribution to journalArticlepeer-review

32 Scopus citations


A density functional theory based computational approach to describing the mechanistic course of the allene azide cycloaddition cascade sequence has been developed. The results of these calculations permit characterization of key reactive intermediates (diradicals and/or indolidenes) and explain the different behaviors observed in the experimental studies between conjugated and nonconjugated species. Furthermore, computational analysis of certain intermediates offer insight into issues of regioselectivity and stereoselectivity in cases where different reaction channels are in competition, suggesting suitable substitutions to achieve a single regioisomer in the indole synthesis via azide-allene cyclization.

Original languageEnglish (US)
Pages (from-to)7638-7646
Number of pages9
JournalJournal of the American Chemical Society
Issue number24
StatePublished - Jun 20 2007

All Science Journal Classification (ASJC) codes

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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