ORGN 317 |
| Construction of spirocyclic centers is a challenging problem in organic synthesis. In this context we have found that appropriately substituted arene-metal complexes can be converted to azaspirocyclic products via net metal mediated dearomatization. Ruthenium (cyclopentadienyl) complexes of benzyl amine derivatives undergo intramolecular nucleophilic aromatic additions to afford Ru-coordinated spirocycles. These spiroheterocyclic ruthenium complexes can then be demetalated under oxidizing conditions to give unique azaspiro[4.5]decane derivatives. The dearomatization leading to the azaspiro compounds can also be achieved via oxidative cyclization using hypervalent iodine reagents. The spirocyclic building blocks obtained by these reactions are amenable to further synthetic manipulations leading to more complex systems.
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Heterocycles and Aromatics
8:00 AM-12:00 PM, Tuesday, March 27, 2007 McCormick Place Lakeside -- Room E350, Level 3, Oral
Division of Organic Chemistry |
