Asymmetric cyclization of nitrogen-containing heterocycles via catalytic C-H bond activation

ORGN 383

Rebecca M. Wilson, Robert G. Bergman, bergman@cchem.berkeley.edu, and Jonathan A. Ellman, jellman@berkeley.edu. Department of Chemistry and Division of Chemical Sciences, Lawrence Berkeley National Laboratory, University of California, Berkeley, Berkeley, CA 94720
A variety of imidazole, benzimidazole, and dihydroquinazoline substrates possessing tethered alkenes were cyclized via C-H bond activation using a rhodium(I)/chiral phosphine catalyst. The reaction was found to proceed in good yield with up to 99% ee at elevated temperatures (135 °C). Ligand optimization and expansion of substrate scope are currently underway.

 

Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Tuesday, August 21, 2007 BCEC -- 253C, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007