Design and Synthesis of Guaianolide Analogs
Asymmetric Allenic Pauson-Khand Reaction (APKR)
Our team designs and synthesizes transition-metal catalysts to control reaction outcomes such as product selectivity and yield. Our approach uses a deep mechanistic understanding informed by a real-time collaboration between experimental and computational organic chemists. In this way, we have synthesized 5,7-ring systems with high enantioselectivity enabled through a stereoconvergent Rh(I)-catalyzed allenic Pauson–Khand reaction. We are applying these findings to the enantioselective synthesis of thapsigargin and we are extending this mechanistic approach to other systems including the PKR of enynes.
Dearomative Cycloaddition Reactions
Our team identifies factors that govern reactivity and product selectivity in the dearomative didehydro-Diels–Alder (DDDA) reaction of heteroarenes. Our approach uses an iterative, real-time collaboration between experimental and computational organic chemists to gain mechanistic insight. We expect that revealing the key reactivity factors will inform other cyclization and cycloaddition reactions involving de-aromatization and re-aromatization processes. Additionally, we are applying these findings to the synthesis of novel ladder-type heteroarene compounds for use in high performing organic photovoltaic materials.