ORGN 142 |
| Aziridines are useful synthetic building blocks and are key features of some natural products. These compounds have been found to be effective anti-tumour agents as well as antibiotics. Aziridine chemistry lags behind that of its oxygen analogue, the epoxide. In particular, there are relatively few methods for asymmetric alkene aziridination. We have been investigating the chemistry of novel chiral aminimines 2 (nitrogen-nitrogen ylides), which can be generated from hydrazinium salts 1 by deprotonation. We have also developed a novel procedure for in situ conversion of a tertiary amine to the hydrazinium salt 1 and alkene aziridination. This procedure avoids the need to separately synthesize and isolate salt 1. Results with a variety of amines, leading to aziridination of enones under mild conditions in good yields will be described. We have also shown that the use of chiral amines allows enantioselective aziridination of chalcones (up to 69% ee).
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Sci-Mix
Division of Organic Chemistry |
