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Enantioselective Copper-Catalyzed 1,3-Dipolar Cycloadditions
Chemical Reviews (2008)
  • Levi M. Stanley
  • Mukund P. Sibi

The addition of a 1,3-dipole to an alkene or alkyne is a prominent transformation in organic synthesis.(1) Over the past two decades the intense study of enantioselective 1,3-dipolar cycloaddition methodologies has provided organic chemists with the tools necessary to synthesize a variety of chiral heterocycles in highly enantioenriched forms.(2) The majority of advances in this area are a direct result of studies focusing on chiral Lewis acid-catalyzed or chiral metal-mediated 1,3-dipolar cycloaddition methodologies. It is important to note that even though the many dipoles possess very strong donor atoms it is still possible to carry out enantioselective Lewis acid-catalyzed dipolar cycloadditions. However, a large number of dipoles require highly basic conditions for their preparation and these conditions could potentially be deleterious for reactions mediated by Lewis acids. Strategies to address these potential drawbacks have been put forth in the literature. One of the more successful strategies among these is dipolar cycloadditions using organocatalysts. Several highly efficient and enantioselective dipolar cycloadditions using different types of organocatalysts have been recently reported in the literature

Publication Date
July, 2008
Publisher Statement
Reprinted (adapted) with permission from Chemical Reviews, 108 (2008): 2887, doi:10.1021/cr078371m. Copyright 2008 American Chemical Society.
Citation Information
Levi M. Stanley and Mukund P. Sibi. "Enantioselective Copper-Catalyzed 1,3-Dipolar Cycloadditions" Chemical Reviews Vol. 108 Iss. 8 (2008)
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