ORGN 105 |
Highly enantioselective copper-catalyzed conjugate addition of diethylzinc to nitroalkenes
| Hojae Choi, Zihao Hua, and Iwao Ojima. Department of Chemistry, State University of New York at Stony Brook, Stony Brook, NY 11794-3400 |
| Copper-catalyzed asymmetric conjugate addition of dialkylzinc to nitroalkenes has been extensively studied because of its utility for the synthesis of a variety of enantiopure synthetic building blocks bearing nitrogen-functional group. However, it has been shown that the enantioselectivity of this reaction is highly dependent on the structure of substrates and varies from moderate to high enatiomeric excess (ee) values. A new class of biphenol-based chiral phosphoramidite ligands developed in our laboratory has been successfully applied to this reaction, showing excellent enantioselectivity for various nitroalkenes. One of the salient features of these monodentate phophoramidite ligands is the fine-tuning capability, which is the key to have achieved high enantioselectivity in this reaction. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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