ORGN 484 |
| Oxazolidinones formed from proline, and aldehydes or ketones are detectable in reaction mixtures involving proline catalysis, where they have previously been considered “parasitic dead ends”. We have already described the isolation and characterization of the oxazolidinone derived from proline and cyclohexanone, as well as its reactions with b-nitrostyrene and chloral (see Helv. Chim. Acta 2007, 90, 425-471). We would like to disclose further NMR studies on the conformation of this oxazolidinone, and on reactions of this intermediate with other electrophiles. We will also discuss the isolation, characterization and reactivity of other oxazolidinones. The stoichiometric reactions of oxazolidinones will all be compared with their catalytic counterparts, and the mechanisms of these reactions discussed. The possible involvement of oxazolidinones and related heterocycles in organocatalysis will be considered.
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Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster
Division of Organic Chemistry |
