Mild Conditions for the Synthesis of Functionalized Pyrrolidines via Pd-Catalyzed Carboamination Reactions

Myra Beaudoin Bertrand, Matthew L. Leathen, and John P. Wolfe*
Department of Chemistry, University of Michigan, 930 N. University Avenue, Ann Arbor, Michigan, 48109-1055
Org. Lett., 2007, 9 (3), pp 457–460
DOI: 10.1021/ol062808f
Publication Date (Web): January 10, 2007
Copyright © 2007 American Chemical Society

Abstract

Abstract Image

The palladium-catalyzed carboamination of N-protected γ-aminoalkenes with aryl bromides and triflates has been achieved under new, mild reaction conditions using the weak base Cs2CO3 in dioxane solvent. These reactions tolerate a wide variety of functional groups, including enolizable ketones, nitro groups, methyl esters, and acetates, which are not compatible with previously described conditions.

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History

  • Published In Issue February 01, 2007
  • Received November 18, 2006

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