The focus of our research program is the development of new organic reactions and their application to the synthesis of therapeutically important compounds. Our efforts are concentrated in several areas:
– Allenyl aldehydes and esters are emerging as valuable intermediates in complex total synthesis especially due to their close association of three functional groups and axial chirality. In this aspect of our research, we utilize inexpensive organo-manganese reagents as auxiliaries to facilitate enantio- and diastereoselective reactions in allene synthesis. We are then fully utilizing these allenes as building blocks in the synthesis of natural products. We have also employed other mechanistically-inspired
• New Reactions with Alkynes – In this project, we explore the reactivity of non-conjugated alkynes in the presence of ammonium salts. These non-metal catalysts promote cyclization reactions to afford medicinally important heterocycles under mild conditions, most likely through a novel ammonium/alkyne cation-pi interaction, which is also being investigated.
• Nucleophilic Fluorination - We are designing new reactions to facilitate radiolabeling with F18 for medical imaging applications (PET). In this regard, we have taken several approaches including the use of chelating leaving groups pioneered in our group that we have termed Nucleophile Assisting Leaving Groups (NALGs). We are also developing novel crown ether-based phase transfer agents that serve as nucleophilic catalysts for various radiofluorination reactions.
• One of our NALG reagents is commercially available at Sigma-Aldrich.
For a less technical description of projects in the group, click here.