Beta-turn peptides as asymmetric catalysts

CHED 529

Michael H. Reutershan, mreuters@bowdoin.edu and Brian R. Linton, blinton@bowdoin.edu. Department of Chemistry, Bowdoin College, 6600 College Station, Brunswick, ME 04011
Asymmetric organocatalysts have been developed that catalyze the reaction of vinyl ketones with nitroalkane derivatives. The peptide catalysts were designed to contain both Bronsted basic and hydrogen-bonding residues located around a central beta-turn core. The mechanism for substrate binding and peptide catalysis will be examined. Additionally, the structural considerations for maximal selectivity will be discussed.