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Rh-Catalyzed C-H Activation Route to Bicyclic Imidazoles
J. C. Rech, M. Yato, D. Duckett, B. Ember, P. V. LoGrasso, R. G. Bergman*, J. A. Ellman*
University of California and Lawrence Berkeley National Laboratory, Berkeley and The Scripps Research Institute, Jupiter, USA
24 April 2007 (online)
A Rh-catalyzed synthesis of aryl-substituted bicyclic imidazoles via C-H activation is described. Using imidazoles with N-chiral appendages, this intramolecular alkylation proceeds smoothly with high enantioinduction and moderate yields to afford the fused imidazoles which are difficult to make, especially with chiral centers at C-7 and C-8 positions. The methyl substitution at C-7 is significant for potent bioactivity.