Allenyl azide cycloaddition chemistry. 2,3-Cyclopentennelated indole synthesis through indolidene intermediates

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

Research output: Contribution to journalArticlepeer-review

35 Scopus citations

Abstract

(Chemical Equation Presented) The thermal, photochemical, and photochemical/CuI-mediated cascade cyclizations of a range of substituted 1-(2-azidophenyl)-3-alkenylallenes are described. These reactions provide both 1,2- and 2,3-cyclopentennelated indole products in varying ratios. In most cases, high regioselectivity for the 2,3-annelated isomer can be achieved under the h?/CuI conditions. Computational studies of this multistep reaction support the intermediacy of indolidene intermediates whose electrocyclizations (with or without copper present) define the regioselectivity branch point in the sequence.

Original languageEnglish (US)
Pages (from-to)4958-4974
Number of pages17
JournalJournal of Organic Chemistry
Volume74
Issue number14
DOIs
StatePublished - Jul 17 2009

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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