Asymmetric acylimidazole alkylation using phase-transfer catalysis

ORGN 505

Merritt B. Andrus, mbandrus@chem.byu.edu, Erik J. Hicken, David K. Bedke, and Michael A. Christiansen, mchristian@chem.byu.edu. Dept. of Chemistry and Biochemistry, Brigham Young U, C100 BNSN, Provo, UT 84602
Past research has resulted in the development of a new methodology for the stereoselective catalytic alkylation of alkoxymethyl aryl ketones. This methodology employs cinchonidine-based, chiral phase-transfer catalysts and has potential for the total syntheses of biologically active targets. These efforts have expanded its scope to the stereoselective alkylation of acyl alkoxy imidazoles. This discovery provides improved access to synthetically useful glycolate structures, bypassing a problematic Baeyer-Villiger oxidation step required previously for aryl ketones. Further developments of this methodology include total syntheses of the biologically active compounds kurasoins A and B.

 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 11 September 2006 Moscone Center -- Hall D, Sci-Mix

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006