ORGN 74 |
Synthesis and catalytic competency of a novel dicationic phase transfer catalyst
| Darren K. MacFarland, Michelle E. Rueffer, and Linda K. Fort. Department of Chemistry, Gettysburg College, 300 N. Washington, Gettysburg, PA 17325 |
| Asymmetric phase transfer catalysis has grown into an important field since O'Donnell's pioneering work in the late 1980's. We describe the synthesis and catalytic competency of a new type of dicationic phase-transfer catalyst based on a tartaric acid core. Similar work by Shibasaki using a different synthetic route was limited in the types of ammonium salts generated, but still gave modest enatioselectivities. Our synthetic route allows for synthesis of a family of related catalyst compounds based on a common intermediate, including secondary and aromatic groups on the nitrogen. Our main application interest is in developing non-natural amino acids; we report asymmetric alkylations and Michael additions to a protected glycine using members of our catalyst family. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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