Synthesis of Optically Pure Fluorosubstituted Isoxazolidines by 1,3-Dipolar Cycloaddition of Nitrones to Chiral Methyl Enol Ethers of 3-Fluoro-1-sulphinyl-2-propanones

Article abstract of DOI:10.1016/S0957-4166(00)80057-9

Optically pure enol ether 4 undergoes 1,3-dipolar cycloaddition, with C,N-diphenylnitrone 5 to give the fluorosubstituted isoxazolidine 6 in a fully regio- and diastereoselective manner.The absolute configuration of 6 has been established by X-ray analysis.When changing the nitrone and/or the fluoro substitution pattern in compounds similar to 4, the same reactivity is observed.