The zwitterionic effect in the stereoselectivity of the reduction of tropinone

ORGN 76

Juliet M. Hahn, jhahn@desu.edu, Ruth Wamwati, and Nicole Morris. Department of Chemistry, Delaware State University, 1200 N. Dupont Hwy, Dover, DE 19901
Stereoselective synthesis in tropinone, a derivative of cocaine is being investigated. Previous work has shown that when a heterocyclic amine is derivatized into a zwitterion, quantitative streoselectivity (greater than 95% of a single isomer) can be achieved. In this work zwitterionic derivatives of tropinone, has been synthesized and fully characterized. The steroselective reduction of the parent tropinone has been completed and characterized. Zwitterionic derivatives of the tropinone has also been reduced by sodium borohydride. The zwitterionic effect will be discussed in controlling stereoselctivity in these reactions. This work is expected to have applications in stereoselective synthesis of potential pharmaceuticals for the class of natural product tropanes.
 

Physical Organic Chemistry, Combinatorial and Process Chemistry, New Reactions and Methodology, Peptides, Proteins and Amino Acids
8:00 PM-10:00 PM, Sunday, April 6, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008