ORGN 51 |
| Satomi Niwayama and Yoshikazu Hiraga. Department of Chemistry, Oklahoma State University, Stillwater, OK 74078-3071 |
| Norbornene derivatives are known to show unique exo facial selectivities in various electrophilic or pericyclic reactions. However, very few examples for such facial selectivities have been reported for reactions that occur away from the norbornane skeleton except for enzymatic reactions. Niwayama recently reported highly efficient selective monohydrolysis of a series of symmetric diesters employing THF and aqueous NaOH solution at 0 degrees. Applying this new monohydrolysis, we found that several exo or endo dimethyl or diethyl bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylates showed higher selectivity toward exo-carboalkoxy groups, despite the fact that the reaction centers are located one carbon unit away from the norbornene rings. Under the reaction conditions, no changes in the stereochemistry of the compounds were observed. To our knowledge, among non-enzymatic reactions, these reactions are the first examples of such unique exo selectivities. |
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New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Organic Chemistry |