Enantioselective 5-<i>exo</i>-Fluorocyclization of Ene-Oximes

Abstract

The enantioselective 5-exo-fluorocyclization of ene-oxime compounds was demonstrated under phase-transfer catalysis. Although deprotonative fluorinations competed, the chemical yields and the ee values of the desired isoxazoline products were generally moderate to good. The absolute stereochemistry of the major isomer was determined to be S by comparison with the literature after transformation of the product to the corresponding iodinated isoxazoline.

Keywords

• fluorine
• asymmetric catalysis
• phase-transfer catalysis
• oxime