A fluorinated porphyrin tweezer: Powerful reporter of absolute configurations for erythro- and threo-diols, amino alcohols and diamines

ORGN 678

Xiaoyong Li, lixiaoyo@msu.edu, Marina Tanasova, tanasova@msu.edu, and Babak Borhan, babak@chemistry.msu.edu. Department of Chemistry, Michigan State University, East Lansing, MI 48824
The absolute configurations of erythro- and threo- diols, amino alcohols and diamines were successfully determined using a highly fluorinated zinc porphyrin tweezer via newly developed chiroptical protocol based on Exciton Coupled Circular Dichroism (ECCD). This novel zinc tweezer host demonstrated good binding affinity with hydroxyl groups due to the greatly enhanced Lewis acidity, thus facilitating the straightforward stereochemical assignment of chiral diols without any derivatization. This method enables the stereochemical determination of erythro diols, which has been problematic via other methodologies. Correlation of the observed CD couplet with the absolute configurations will be presented.
 

Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, March 26, 2007 Hyatt Regency Chicago -- Riverside Center, Sci-Mix

Division of Organic Chemistry

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