ORGN 115 |
| Diels-Alder reactions induced by electron transfer exhibit high stereospecificity in the formation of diastereomeric products. At the same time, the high energy radical cation intermediates react many orders of magnitude faster than their neutral counterparts. The structure and reactivity of these radical cations is controlled by factors that are very different than for the case of their neutral counterparts, such as reaction dynamics, ion-molecule complexes and conjugation. With a detailed understanding and application of these factors, higher reactivity and selectivity could be achieved. Here, we present the first systematic study of diastereoselectivity of electron transfer catalyzed Diels-Alder reactions. The manipulation of conditions in the electron transfer catalyzed reaction of phellandrene with donor and acceptor substituted styrenes produces different ratios of diastereomers.
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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
Division of Organic Chemistry |
