Catalytic enantioselective alpha-oxytosylation of propiophenone using chiral hypervalent iodine reagents

CHED 533

Shauna M. Paradine, smp12@albion.edu1, Andrew N. French, afrench@albion.edu1, T. Keri Page2, Robert D. Richardson2, and Thomas Wirth, WIRTH@CF.AC.UK2. (1) Department of Chemistry, Albion College, Albion, MI 49224, (2) School of Chemistry, Cardiff University, Park Place, Cardiff CF10 3AT, United Kingdom
We report herein our initial results of the catalytic enantioselective alpha-oxytosylation of propiophenone using chiral hypervalent iodine reagents. Low to moderate enantioselectivities of the alpha-oxytosylate are seen using a variety of ortho substituted chiral aryl iodides as catalysts. We also report our efforts using a variety of co-oxidants and reaction conditions in order to optimize this reaction. To our knowledge, this represents the first example of enantioselective organocatalysis using hypervalent iodine reagents.

 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Division of Chemical Education

The 233rd ACS National Meeting, Chicago, IL, March 25-29, 2007