ORGN 524 |
| Reaction of a Lewis acid-activated imino ester and phenyldiazomethane at low temperature yields a mixture of aziridines (predominantly cis) without the usual enamino ester byproducts. Interestingly, while allowing the crude to warm-up after consumption of the imine, an in situ decomposition of the trans-aziridine occurs and the imino ester reforms. The imine is recycled when it reacts with the excess phenyldiazomethane; the result is a boost to the yield of cis-aziridine. These reactions proceed with excellent conversion of starting materials and afford a high yield of aziridine.
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New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
