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Article
Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates
Journal of the American Chemical Society (2010)
  • Levi M. Stanley, University of Illinois at Urbana-Champaign
  • Chen Bai, University of Illinois at Urbana-Champaign
  • Mitsuhiro Ueda, University of Illinois at Urbana-Champaign
  • John F. Hartwig, University of Illinois at Urbana-Champaign
Abstract

Versatile methods for iridium-catalyzed, kinetic asymmetric substitution of racemic, branched allylic esters are reported. These reactions occur with a variety of aliphatic, aryl, and heteroaryl allylic benzoates to form the corresponding allylic substitution products in high yields (74−96%) with good to excellent enantioselectivity (84−98% ee) with a scope that encompasses a range of anionic carbon and heteroatom nucleophiles. These kinetic asymmetric processes occur with distinct stereochemical courses for racemic aliphatic and aromatic allylic benzoates, and the high reactivity of branched allylic benzoates enables enantioselective allylic substitutions that are slow or poorly selective with linear allylic electrophiles.

Disciplines
Publication Date
June, 2010
Publisher Statement
Reprinted (adapted) with permission from Journal of the American Chemical Society 132 (2010): 8918, doi:10.1021/ja103779e. Copyright 2010 American Chemical Society.
Citation Information
Levi M. Stanley, Chen Bai, Mitsuhiro Ueda and John F. Hartwig. "Iridium-Catalyzed Kinetic Asymmetric Transformations of Racemic Allylic Benzoates" Journal of the American Chemical Society Vol. 132 Iss. 26 (2010)
Available at: http://works.bepress.com/levi_stanley/13/