ORGN 109 |
| The ozonolysis of alkenes is a very powerful reaction which is widely used in organic chemistry. The majority of ozonolysis reactions provide either stable secondary ozonides or nucleophilic addition products. In 1985 Kuczkowski et al. demonstrated that the ozonolysis of ethyl vinyl ether in non-polar solvents occurs via an unusual mechanism whereby the carbonyl oxide undergoes preferential cycloaddition to the unreacted vinyl ether instead of the newly created formate ester to generate a 3-alkoxy-1,2-dioxolane. We have found that this reaction is broadly applicable to a range of substituted vinyl ethers, and that the in-situ acid catalyzed rearrangement of the dioxolane provides the substituted β-hydroxy esters in good yield. We have applied this methodology in our approach to the synthesis of the bruchin family, potent insect derived plant regulators. Finally, we have also shown that dioxolanes formed from racemic vinyl ethers undergo modest kinetic resolution to generate enantiomerically enriched β-hydroxy esters. |
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Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster
Division of Organic Chemistry |