Stereoselective Reactions of Aromatic Building Blocks

With the support of the Chemical Synthesis program in the Division of Chemistry, Professor Jeffrey Johnson of the University of North Carolina at Chapel Hill will study the reaction chemistry of abundant aromatic starting materials. Molecular complexity and sustainability are considerable challenges for the field of chemistry. Professor Johnson and his team are seeking to develop new chemical reactions that generate highly functionalized and useful products from simpler and abundant feedstock chemicals. It is expected that some of the highly functionalized products will find applications as bioactive compounds in chemical biology and medicinal chemistry. Catalysis will play a central role in these studies, which are expected to provide new experimental tools for the chemical community. The research impacts will be complemented by the research team’s efforts in outreach to elementary schools and the general public, and through support for students from underrepresented groups in science, technology, engineering and mathematics (STEM). The generation of highly functionalized and stereochemically defined small molecule building blocks is central to many scientific endeavors, particularly in the realm of chemical synthesis for applications in chemical biology. Aromatic compounds are seldom viewed as useful starting molecules for stereoselective synthesis of nonaromatic materials due to their inherent stability and relative inertness. Professor Johnson’s team is pursuing a multipronged approach to the development of catalytic pathways that convert achiral aromatic starting materials into useful, stereoenriched, chiral building blocks, including highly functionalized systems and heterocycles. The Johnson laboratory aims to transform achiral aromatic compounds into chiral carbocycles through catalyzed dearomatization reactions such as carbenoid transfer and reduction under mild conditions. Application to the rapid generation of natural products and natural product mimics is expected during the course of these studies. This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.