ORGN 396 |
| Recent reports have shown that the use of cyclic five membered nitrogen containing heterocycles as catalysts for the iminium ion catalysed Diels-Alder, [3+2] and [4+3]-cycloadditions, as well as Michael additions of pyrroles, anilines, nitroalkanes, malonates and hydride have met with remarkable levels of asymmetric induction. We have become interested in developing new catalyst architectures to accelerate this class of transformation with the ultimate aim of providing more efficient systems than those reported. Our approach resides in gaining a fundamental mechanistic understanding of the reaction and applying this knowledge to improve catalytic efficiency. Utilising a combination of molecular modelling, kinetic investigations and solid-state structural analysis we have probed the catalytic cycle of the iminium ion catalysed Diels-Alder cycloaddition reaction. This talk will describe our results in each of these areas and ongoing efforts in using these to develop a predictive tool for catalyst activity in this fascinating class of chemical transformation.
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Physical Organic Chemistry: Calculations, Mechanisms, Photochemistry, and High Energy Species
8:00 AM-11:40 AM, Tuesday, August 21, 2007 BCEC -- 254 A/B, Oral
Division of Organic Chemistry |
