Catalytic ephedra ligands for asymmetric 1,2-additions and conjugate additions: Efforts toward the asymmetric synthesis of tolterodine

CHED 534

Melissa A. Dean, madean@ilstu.edu and Shawn R. Hitchcock, hitchcock@ilstu.edu. Department of Chemistry, Illinois State University, Campus Box 4160, Normal, IL 61790-4160
The use of catalytic asymmetric methods in organic chemistry remains as an important aspect of organic chemistry. Our research program is focused on developing new templates for conducting asymmetric syntheses. We have used enantiomerically enriched ephedrine and pseudoephedrine to create a series of ligands that have shown promise in catalyzing the 1,2-addition of diethylzinc to aldehydes. The pathway for the preparation of these ligands involves alkylation of β-aminoalcohol with a variety of bromoacetaldehyde acetals. This presentation will describe the details of the research that has been conducted as well as efforts directed towards the asymmetric synthesis of tolterodine. Tolterodine is a pharmaceutical agent that is used by persons who suffer from urinary incontinence, which is defined as the inability to control the flow of urine and the involuntary action of urination. The poster will describe the effectiveness of using the Ephedra ligands in asymmetric conjugate addition in the pursuit of tolterodine.