ORGN 100 |
Diastereoselective indium-mediated allylation of chiral hydrazones
| Gregory R. Cook1, Bikash Maity2, and Robert Kargbo2. (1) Department of Chemistry, North Dakota Network in Catalysis, North Dakota State University, Ladd Hall, Fargo, ND 58105, (2) Department of Chemistry and Molecular Biology, North Dakota State University, Ladd Hall, Fargo, ND 58105 |
| Chiral amines containing an allylgroup are very useful for subsequent synthetic manipulation in the synthesis of important biologically active compounds. We have investigated indium(0)-mediated diastereoselective allylation of chiral hydrazones derived from both aromatic and aliphatic aldehydes. In the selection of chiral auxiliary (Xc.) we have screened several oxazolidinones with p-tolyl hydrazones. We have extensively studied allylation on substrates prepared from valinol derived chiral auxiliary and different aldehydes. Excellent diastereoselectivity was obtained for the hydrazones derived from aromatic aldehydes and hydrazones derived from aliphatic aldehydes provided excellent diastereoselectivity in the presence of indium(III)triflate.The result of these studies and recent advances in asymmetric indium chemistry will be presented. 
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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
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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