CHED 814 |
| Keiko F. Duff1, Richard Berger2, and James L. Leighton2. (1) Department of Chemistry and Physics, Saint Mary's College, 1315 E. Victoria, South Bend, IN 46614, (2) Department of Chemistry, Columbia University, 3000 Broadway, Havemeyer Hall, Mailcode-3166, New York, NY 10027 |
| (S,S)-pseudoephedrine derived allylsilacyclopentane reagent reacted with ketone-derived benzoylhydrazones in the absence of catalyst to produce homoallylic hydrazides in high yield and substantial ee. It was found that hydrazones with electron-withdrawing substituents gave the best results, whereas those with electron-rich substituents resulted in low yields and/or low enantioselectivities. In addition, N-N bond cleavage can be performed via simple addition of samarium(II)iodide. This provides a useful and efficient method for synthesizing enantiomerically pure homoallylic amines with an α-quaternary center, which have been difficult targets in the past. |
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Undergraduate Research Poster Session: Organic Chemistry
2:00 PM-4:00 PM, Monday, March 29, 2004 Anaheim Convention Center -- Hall A, Poster
Division of Chemical Education |