ORGN 388 |
| In recent years, ynamides chemistry has emerged as a field of interest for the development of new synthetic methodologies. Here, we report a transition metal catalyzed [4 + 2] cycloaddition reaction of chiral ynamides. Upon treatment with Wilkinson's catalyst [20 mol%], a chiral ynamide and an appropriate diene undergoes an intermolecular [4 + 2] cycloaddition in toluene at 110 oC, followed by aromatization, give highly substituted aromatic system in good yields with a modest atropisomeric selectivity, while a chiral ynamide tethered to a 1,3-butadiene undergoes a highly diastereoselective intramolecular cycloaddition to give the respective nitrogen heterocycle in high yields as a single isomer.
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Bioorganic, Metal-Mediated Reactions, and Molecular Recognition
8:00 PM-10:00 PM, Tuesday, 30 August 2005 Washington DC Convention Center -- Hall A, Poster
Division of Organic Chemistry |
