ORGN 121 |
| Copper (II) complexes 2 with hexafluoroantimonate counterion were found to promote a Wagner-Meerwein rearrangement process of ?-keto ester substrate 1.The reaction gave either spiro products 3 or 4 exclusively, depending on the nature of R group. Only one diastereomer was observed in each case. If catalyst loading was reduced, the Nazarov cyclization products 5 could be obtained. The concentration dependence will be discussed, as well as the importance of ligand, metal and counterion on reaction pathway. Progress toward enatioselective rearrangements will also be presented.
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Process R&D, Physical Organic Chemistry, Heterocycles, Aromatics, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, March 25, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Sci-Mix
Division of Organic Chemistry |
