Development of novel ligands for asymmetric oxidative biaryl coupling and asymmetric ketoester alkylation

ORGN 299

Marisa C. Kozlowski, Department of Chemistry, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, PA 19104
We have been engaged in the development of computational methods to aid in the identification of new catalysts for asymmetric synthesis. An overview of these methods will be presented with an emphasis on recent efforts which have shown that quantitative structure selectivity relationships (QSSR) can be generated for chiral catalysts. In these studies, the quantum chemical environment defined by each ligand is determined, and structural features which correlate with reaction selectivity are identified using linear regression analyses. Examples of catalysts developed using these tools will be presented in the context of 1,5-diaza-cis-decalin copper catalysts for enantioselective oxidative biaryl coupling and bifunctional aminosalen catalysts for the enantioselective alkylation of alpha-ketoesters.