ORGN 638 |
| The stereochemistry of the migrating carbon in the photo-Favorskii rearrangement of α-substituted p-hydroxybutyrophenones has been investigated for a series of diastereomeric carboxylates and sulfonates. Positioning the leaving group on a stereogenic center provides an opportunity to probe steric factors and the stereochemical consequences of the rearrangement to the p-hydroxyphenylbutanoic acid. Questions regarding substrate-chromophore recombination, configurational relaxation, and enantiomeric configuration and purity of the rearranged chromophore have been addressed. Comparative quantum yields of the diastereomeric pairs in various solvent systems have been investigated as well as the preparative synthetic routes to homochiral p-hydroxybutyrophenone-protected carboxylates will be presented.
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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 |
