Synthesis of chiral N-alkoxybenzohydroximoyl halides

CHED 482

Greg M. Landry, greg.landry@selu.edu, Brittany R. Williams, brittany.williams-3@selu.edu, Tiffany E. Thomas, tiffany.thomas@selu.edu, and Debra D. Dolliver, ddolliver@selu.edu. Department of Chemistry & Physics, Southeastern Louisiana University, SLU 10878, Hammond, LA 70402

Benzohydroximoyl halides have been used in synthetic schemes to produce oxime ethers of predictable E or Z stereochemistry.  We now report the synthesis of benzohydroximoyl halides of specific E or Z configuration containing a chiral N-alkoxy group.  These compounds are produced by synthesizing a chiral N-alkoxyphthalimide via a Mitsunobu reaction.  N-alkoxylamine is released from the phthalimide and reacted with benzoyl chloride to produce a chiral benzohydroxamate.  This hydroxamate can then be converted to a chiral hydroximoyl halide.  The stereochemistry of the resulting benzohydroximoyl halide will be discussed along with potential reaction schemes to convert it to a chiral oxime ether.