ORGN 51 |
| The cationic aza-Cope rearrangement—Mannich cyclization is a tandem reaction sequence that has been used to efficiently and stereoselectively synthesize functionalized pyrrolidines. However, a major disadvantage associated with this sequence is that lengthy reaction times are typically required when iminium cation formation proceeds via aldehyde condensation with a free amine. In our laboratories, we are attempting to shorten the reaction time of the aza-Cope—Mannich reaction by developing the first microwave-assisted version of this reaction. By contrast to conventional heating methods which require up to 48 hours of reaction time, we have demonstrated that microwave energy can be used to generate pyrrolidines in a matter of minutes (Scheme). Details of the experimental conditions, comparisons between microwave and conventional heating yields and stereoselectivities will be presented.
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Heterocycles and Aromatics
1:00 PM-5:20 PM, Sunday, 26 March 2006 Georgia World Congress Center -- C301, Oral
Division of Organic Chemistry |
