Benedictine University, Chemistry, Lisle, IL 60532
Enantiopure Wieland-Miescher ketone is accepted as a useful synthon for the construction of steroids, terpenoids, and taxol. Previous research has shown L-Proline to be an effective catalyst in the asymmetric synthesis of enantiopure WMK through a one-pot Robinson annulation reaction. Although L-Proline enatioselectively catalyzes the formation of WMK, it is still not an ideal catalyst. The reaction is substrate specific and there is a non-ideal reaction time of about 90 hours. Substantial benefit would result from a more effective catalyst; for this reason, alternatives to L-Proline need to be employed. MacMillan’s chiral amine organocatalysts have proven effective at similar types of reactions and therefore are considered as alternative catalysts. Other chiral amine catalysts with similar traits are also explored.
[Abstract (DOC)]