ORGN 586 |
| Madhuri Manpadi and Alexander Kornienko. Department of Chemistry, New Mexico Institute of Mining and Technology, 801 Leroy Place, Socorro, NM 87801 |
| The high anti-selectivities in the addition of organocopper reagents to γ-alkoxy-α,β-enoates are well precedented, but the examples of arylcuprate reagents are limited. In the course of our work directed towards the total synthesis of an anti-tumor alkaloid pancratistatin, we observed very high selectivities of the addition of various arylcuprates to γ, δ, ε-trialkoxyenoates. To understand the stereochemical outcome of these reactions and the importance of δ, ε-alkoxy groups we have systematically evaluated selectivities of arylcuprate conjugate additions to model trans and cis γ-alkoxyenoates. The observed selectivity trends are readily explained on the basis of a modified Felkin-Anh hypothesis and/or the Cieplak effect. |
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New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry |