Cyclization Cascade of Allenyl Azides: Synergy Between Theory and Experiment

Author(s): Olalla Nieto Faza, Ken S. Feldman, Carlos Silva Lopez.

Journal Name: Current Organic Chemistry

Volume 14 , Issue 15 , 2010

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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 Curtin- Hammett 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.

Keywords: Allenyl azide, azatrimethylenemethane, indole, DFT, rationalization, Curtin-Hammett model, Indolidene intermediates, Curtin-Hammett regime, Diradical-mediated reactions, Trimethylenemethane (TMM) diyl, Triazoline intermediate, Regioslectivity, Anisotropy of the current induced density (ACID), Allenyl azide cyclization chemistry

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Article Details

Year: 2010
Page: [1646 - 1657]
Pages: 12
DOI: 10.2174/138527210793563305
Price: $58

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