ORGN 736 |
| Trifluoromethyl-containing organic compounds have attracted much attention because of their application in the field of medicinal and agrochemical chemistry. Among a variety of approaches available for the synthesis of the α-trifluoromethyl alcohols, enantioselective nucleophilic trifluoromethylation of carbonyl compounds using the Ruppert-Prakash reagent, (trifluoromethyl)trimethylsilane, Me3SiCF3, is surely the most straightforward operation for construction of the corresponding chiral molecules. Recently, we disclosed the highly enantioselective trifluoromethylation of aryl ketones with Me3SiCF3 catalyzed by a combination of ammonium bromides derived from cinchona alkaloids and tetramethylammonium fluoride (TMAF). However this method was not effective for the enantioselective trifluoromethylation of aldehydes, and all of the previous reports for enantioselective trifluoromethylation including our results, phase-transfer catalysts have been used. We attempt herein the enantioselective trifluoromethylation of carbonyl compounds by the use of chiral crown ethers. |
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Heterocycles and Aromatics, Asymmetric Reactions and Syntheses and Total Synthesis of Complex Molecules
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Ballroom C, Poster
Division of Organic Chemistry |