Dr. Rebecca Davis is an organic chemist at The University of Manitoba. Her research is focused on exploring of the mechanisms of asymmetric organocatalytic reactions and broadening the range of organic reactions in which asymmetric organocatalysis can be applied. Dr. Davis current research topics include: mechanisms in asymmetric phase transfer catalysis; counter-ion interactions in non-covalent organocatalysis; and development of stereoselective rearrangement reactions. Dr. Rebecca Davis obtained her Ph.D at the University of California, Davis, and conducted Postdoctoral Research at The Centre for Catalysis at Aahus University.
Professor of Organic Chemistry, Computational Chemistry
Department of Chemistry, University of Manitoba
“There and Back Again: A Tale of Stereoselectivity in Aminocatalysis”
Asymmetric aminocatalysis has attracted attention as a catalytic method in large part due to their potential for high stereoselectivity. This is typically attributed to the difference in activation energy of the diastereomeric transition states in the addition of the nucleophile to the carbonyl species. However, little attention has been paid to the role of thermodynamics in these systems in regard to the relative stabilities of intermediates that lie downstream of the addition step. Recent mechanistic work and reports of unexplained selectivity patterns suggest that these downstream intermediates may play a significant role in determining stereoselectivity. This lecture will discuss our efforts to provide fundamental insight into the mechanisms of asymmetric aminocatalysts with a focus on determining the origin of enantioselection.