Progress toward the synthesis of a 1-iodo-2-naphthol-based chiral hypervalent iodine reagent

CHED 417

Ryan Stowe, Chemistry, Albion College, 611 E. Porter St., Albion, MI 49224 and Andrew N. French, afrench@albion.edu, Department of Chemistry, Albion College, 611 E. Porter St, Albion, MI 49224.
Hypervalent iodine reagents are useful in a wide variety of reactions including oxidations, lactonizations, additions, and rearrangements. The French lab has synthesized a number of chiral, asymmetric hypervalent iodine compounds for use in enantioselective additions. The most successful of these compounds was able to attain an enantiomeric excess of 65% in additions to monosubstituted alkenes. Last year, it was determined that these hypervalent iodine reagents may be used catalytically in oxytosylation reactions of enolizable ketones. Also, with prior reagents it was noted that changing the substituent ortho to the iodine improved selectivity. Therefore, to improve the EE of the catalytic process, new hypervalent iodine reagents must be developed. We report here on our continued efforts in the synthesis of a 1-iodo-2-naphthol – based chiral hypervalent iodine reagent, 1.