My research broadly deals with the areas of methodology development and natural product synthesis. Recent work has focused on the use of ozone to generate carbonyl oxides.
These reactive intermediates have not been widely studied, but provide access to an array of structurally unique compounds when reacted with suitable nucleophiles or 1,3-dipolarophiles.
Recent projects include the development of a novel method for the synthesis of aldehyde-ester-alkene containing compounds in one step from the ozonolysis of cycloalkenes. This methodology has been adapted and used in a short synthesis of phoracantholide I, a defensive secretion from the eucalypt longicorn beetle. Using a similar strategy a total synthesis of jasmine ketolactone is currently underway.
We are also investigating the ozonolysis of vinyl ethers. In the presence of nonpolar solvents such as hexanes the primary ozonide resulting from ozonolysis of the vinyl ether decomposes to an unsubstituted carbonyl oxide and a formate ester. Under the reaction conditions the carbonyl oxide preferentially undergoes [3+2] cycloaddition to the unreacted vinyl ether to generate 3-alkoxy-1,2-dioxolanes in near quantitative yield.
We have shown that if a chiral acid catalyst is used these useful intermediates can be ring opened in a kinetic resolution process to provide optically active dioxolanes and hydroxy esters.