ORGN 9 |
| The application of chiral catalysts upon chiral substrates can provide various products. The reaction may be governed by the predisposition of the substrate itself, or by a matched or mismatched case of catalyst control. L,L-Di-myo-inositol-1,1'-phosphate is a natural product with thermostabilizing properties in Archaea. It is our goal to synthesize this molecule convergently using a chiral phosphoryl chloride and a pro-chiral alcohol. We plan to study the stereochemical outcome of this reaction when phosphorylation peptide catalysts previously developed in the Miller laboratory are used on these systems, namely, will the reaction proceed through substrate control, catalyst control, or both? We anticipate that the peptides may interact in a matched case, enhancing selectivity, or a mismatched case, reversing selectivity. These experiments will give us valuable insight into the substrate scope of peptide-catalyzed chiral phosphoryl transfer reactions. |
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Asymmetric Reactions and Syntheses
8:00 AM-12:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Rm. R06, Oral
Division of Organic Chemistry |