Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved Regioselectivity

Ken S. Feldman,*† D. Keith Hester II,† Carlos Silva López,‡ and Olalla Nieto Faza‡
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, Departmento de Quimica Organica, Universidade de Vigo, Lagoas Marcosende, 36200 Vigo, Galicia, Spain, and Department of Chemistry, University of Minnesota, 207 Pleasant Street SE, Minneapolis, Minnesota 55455-0431
Org. Lett., 2008, 10 (8), pp 1665–1668
DOI: 10.1021/ol800429j
Publication Date (Web): March 18, 2008
Copyright © 2008 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Pennsylvania State University.

,
‡

 Universidade de Vigo and University of Minnesota.

, ksf@chem.psu.edu

Abstract

Abstract Image

Irradiation of 2-(3-alkenyl)allenylphenyl azides in the presence of excess CuI furnished functionalized 2,3-cyclopentenylindoles in good yield with only trace amounts of competitive C−N-bonded regioisomeric products. These results represent a significant departure from the modest-to-nonexistent regioselectivity that attended thermal cyclization of these allenyl azide substrates.

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History

  • Published In Issue April 17, 2008
  • Received February 25, 2008

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