ORGN 361 |
| The development of new asymmetric catalysts continues to be an important topic in the field of organic chemistry. Amino acids and short peptide sequences that function as asymmetric catalysts for a variety of reactions have been well documented. Previous research in our group has demonstrated that amino acid and peptides-bound borate counteranions can be readily prepared from amino acids or peptides and tartaric acid, and their ion pairing to copper (I) cations can induce asymmetry into metal-catalyzed reactions. Considering the structural flexibility of peptides, this provides a straightforward and modular non-bonding method to incorportate chirality into catalysis. This poster will describe our synthesis and characterization of a new class of metal-free proton acids associated to amino acid and peptide-based chiral borate anions as a potential new class of acid catalysts. These acids can be readily generated from peptide-tethered diols, and have been examined for their ability to induce asymmetry into aza Diels–Alder and aldol–type reactions.
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Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
