New methods for mechanistic inquiry into asymmetric reactions

ORGN 225

Matthew P. Meyer,, School of Natural Sciences, University of California, Merced, 4225 N. Hospital Rd., Atwater, CA 95355
Asymmetric reactions are playing an increasing role in pharmaceutical production processes. Surprisingly, few quantitative methods exist for probing this interesting class of reactions. In this talk, I will present a new suite of mechanistic methodologies that are designed to interrogate the symmetry breaking process inherent to asymmetric reactions. Principal among these methodologies is a suite of kinetic isotope effect (KIE) methods collectively known as symmetry-adapted KIEs (SAKIEs). Two varieties of SAKIEs have been developed: 1) KIEs that probe symmetry breaking among enantiotopic groups and 2) KIEs that probe symmetry breaking among homotopic groups. The former technique has been successfully used to probe the role of non-bonding interactions that develop in the transition states of stereoselective reductions. The latter technique has the added advantage that it can be used in reactions that have multiple reaction channels. Results from investigations of stereoselective reductions and organocatalytic aldol reactions will be presented.

Young Academic Investigators
8:00 AM-12:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- 207A, Oral

Division of Organic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009