Synthesis of organocatalysts for asymmetric Robinson annulations

CHED 493

Sarah E. St. John, sarah_st.john@ben.edu, Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas, cmascarenhas@ben.edu. Department of Chemistry, Benedictine University, 5700 College Road, Lisle, IL 60532
Enantiopure Wieland-Miescher ketone (WMK) is accepted as a useful synthon for the construction of steroids, terpenoids, and taxol. Previous research has shown L-Proline to be a moderately effective catalyst in the asymmetric synthesis of WMK through a one-pot Robinson annulation although the reaction is sluggish. Substantial benefit would result from a more effective catalyst; for this reason, alternatives to L-Proline need to be employed. MacMillan's catalysts as well as other organocatalysts have proven effective at similar types of reactions and are therefore considered as potential catalysts for Robinson annulations. Results from our studies of various catalysts, including their synthesis, the effect of solvent and catalyst structure on enantioselectivity and product yield are reported.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

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