Amino acid derived benziodazoles: New chiral hypervalent iodine reagents

ORGN 638

Alexey Y. Koposov, Brian Netzel, and Viktor V. Zhdankin. Department of Chemistry, University of Minnesota Duluth, 10 University Drive, Duluth, MN 55812
In the last 20 years, the hypervalent iodine compounds gained importance as an alternative to the transition metal reagents for various organic transformations. Among these compounds, trivalent iodine reagents (such as iodobenzene diacetate and derivatives of benziodoxole) were found to be a useful tool for oxidation of phenols, oxidative cyclizations, and introduction of functional groups. However the lack of chirality in these reagents significantly restricts their application in organic synthesis. In this presentation, the recent progress on the preparation of chiral hypervalent iodine reagents will be demonstrated. These chiral reagents are based on the amino acid derived benziodazoles 1 with various functional groups attached to the hypervalent iodine center. The new benziodazoles 1 are potentially useful reagents for the transfer of the functional group to organic substrates.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004