ORGN 167 |
| The selective coupling of ketones and N-tosyl-protected aziridines can be carried out efficiently in the presence of a catalytic amount of Sc(OTf)3. Oxazolidines are produced in up to 98% yield and 100:1 selectivity from the preferential opening of one the aziridine N—C bonds. Optimization of the conditions of this reaction has been undertaken for temperature, solvent, and substrate concentration. Facile reactions can be carried out with aliphatic and aromatic ketones, as well as ketones containing substituted Α,Β olefins and acetylenes. A variety of tosyl-protected aziridines containing aromatic and aliphatic functionality, electron-withdrawing and donating groups, as well bulky groups can be readily incorporated.
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Combinatorial, Parallel, and Solid-Phase Chemistry
8:00 PM-10:00 PM, Sunday, 10 September 2006 Moscone Center -- Hall D, Poster
Division of Organic Chemistry |
