CHED 795 |
| Kelsey L. Hanson and William Dasher. Department of Chemistry, University of Puget Sound, 1500 North Warner, Tacoma, WA 98416 |
| The enantioselective synthesis of Michael reaction products with various adducts using the cinchona alkaloid quinine and hydride reagent Red-Al as a catalyst are reported. The quinine/Red-Al complex was prepared in a 10% load in situ with the enone and adduct added in stoichiometric amounts to give yields of up to 99.1% of the ketone product. The ketone enantiomers did not efficiently separate on a chiral GC column; however, conversion to a diastereomeric ketal via a microscale reaction using (2R,3R)-butane-diol resulted in near baseline separation of the two diastereomers on a non-polar capillary column. Modest enantiomeric excesses, up to 27%, were achieved using the underivatized quinine/Red-Al complex. Synthesis and results using new derivatized complexes are ongoing. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |