Cyclization cascade of allenyl azides: Synergy between theory and experiment

Olalla Nieto Faza, Ken S. Feldman, Carlos Silva López

Research output: Contribution to journalArticle

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Abstract

Collaborative work between experimentalists and computational chemists have demonstrated a stong synergy which allowed the rationalization of allenyl azide chemistry and permited the development of an efficient synthetic tool aimed at the preparation of several alkaloids. Saturated allenyl azides undergo a reaction cascade involving key diradical intermediates that follow the CurtinHammett model whereas unsaturated allenyl azides form indolidene intermediates that furnish the final indole products via electrocyclic ring closure events taking place out of the Curtin-Hammett regime. The regiochemistry of the reaction cascade with the latter substrates can be manipulated by Cu(I) addition to the reaction mixture.

Original languageEnglish (US)
Pages (from-to)1646-1657
Number of pages12
JournalCurrent Organic Chemistry
Volume14
Issue number15
Publication statusPublished - Sep 14 2010

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All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

Faza, O. N., Feldman, K. S., & López, C. S. (2010). Cyclization cascade of allenyl azides: Synergy between theory and experiment. Current Organic Chemistry, 14(15), 1646-1657.