Zinc-mediated chain extension: Stereoselective approach to ketomethylene isosteres

ORGN 320

Charles K. Zercher, Weimin Lin, wlin@cisunix.unh.edu, and Fan Su. Department of Chemistry, University of New Hampshire, Durham, NH 03824
A zinc carbenoid-mediated chain extension reaction is used to generate ketomethylene isosteric replacements for peptide bonds. Tandem chain extension-aldol reactions and tandem chain extension-homoenolate generation reactions are used to incorporate mimics of amino acid side chains. Identification of the stereoselectivity of the aldol reaction was established through application of a novel CAN-mediated oxidative cyclization.