Prev. Article Next Article Table of Contents

Communication

Allenyl Azide Cycloaddition Chemistry. Synthesis of Pyrrolidine-Containing Bicycles and Tricycles via the Possible Intermediacy of Azatrimethylenemethane Species

Supporting Info

Ken S. Feldman* and Malliga R. Iyer

Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802

J. Am. Chem. Soc., 2005, 127 (13), pp 4590–4591

DOI: 10.1021/ja050757w

Publication Date (Web): March 10, 2005

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

, ksf@chem.psu.edu

Abstract

Thermolysis of 5-azidoallenes bearing a C(1) methyl group and either an aryl ring or an alkene on C(1) furnishes tricyclic (from the aryl substrates) or bicyclic (from the alkenyl substrates) pyrrolidine products following formal H−CN addition across an intermediate imine. High levels of diastereoselectivity are observed in all cases studied. This reaction cascade presumably passes through unobserved triazoline and azatrimethylenemethane diyl intermediates en route to product.

View: Full Text HTML | Hi-Res PDF

Tools

SciFinder Links

History

Published In Issue April 06, 2005
Received February 4, 2005

Recommend & Share

Related Content

Cyclization Cascade of Allenyl Azides: A Dual MechanismJournal of the American Chemical Society
- Cyclization Cascade of Allenyl Azides: A Dual Mechanism
  Carlos Silva López, Olalla Nieto Faza, Ken S. Feldman, Malliga R. Iyer, and D. Keith Hester II
  Journal of the American Chemical Society 2007 129 (24), pp 7638–7646
  Abstract: 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 (...
  Abstract | Full Text HTML | Hi-Res PDF
Allenyl Azide Cycloaddition Chemistry. Photochemical Initiation and CuI Mediation Leads to Improved RegioselectivityOrganic Letters
- 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
  Organic Letters 2008 10 (8), pp 1665–1668
  Abstract: 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 ...
  Abstract | Full Text HTML | PDF w/ Links | Hi-Res PDF
Construction of Azacycles Based on Endo-Mode Cyclization of AllenesThe Journal of Organic Chemistry
- Construction of Azacycles Based on Endo-Mode Cyclization of Allenes
  Chisato Mukai, Minoru Kobayashi, Shoko Kubota, Yukie Takahashi, and Shinji Kitagaki
  The Journal of Organic Chemistry 2004 69 (6), pp 2128–2136
  Abstract: A new procedure for constructing monocyclic five- and six-membered azacycles by the endo-mode ring-closing reaction of allenylazido derivatives under neutral conditions has been developed. The azabicyclo[m.n.0] compounds were prepared by applying this ...
  Abstract | Full Text HTML | Hi-Res PDF

Communication

Allenyl Azide Cycloaddition Chemistry. Synthesis of Pyrrolidine-Containing Bicycles and Tricycles via the Possible Intermediacy of Azatrimethylenemethane Species

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Cyclization Cascade of Allenyl Azides: A Dual Mechanism

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

Construction of Azacycles Based on Endo-Mode Cyclization of Allenes

Other ACS content by these authors:

JOURNALS

BOOKS

MAGAZINE

COMMUNITIES

DIRECTORIES & DATABASES