Professor Joseph Topczewski
Azides and heterocycles: Fun with dynamic chemistry and reactive intermediates
Chiral amines and heterocycles are ubiquitous motifs in chemical synthesis. The efficient synthesis of certain chiral amines and heterocycles remain a tremendous challenge. Presented herein is an unusual approach to chiral amine synthesis that utilizes the spontaneous rearrangement of allylic azides (Winstein Rearrangement). One component of the equilibrating mixture can be selectively trapped, establishing the amine bearing stereocenter. However, accomplishing this in practice requires high levels of selectivity and the simultaneous application of numerous control elements. Approaches to enabling selectivity will be described along with synthetic applications of the reactions, including in the synthesis of heterocyclic products.
Professor Joseph Topczewski's research lab aims to invent transformative synthetic methods to reduce chemical waste generation, while simultaneously redefining how chemists approach making medicines. His researcher discovers and optimizes innovative synthetic methods to address this 21st century challenge. Superior methods i) prevent unnecessary resource consumption, ii) minimize the generation of chemical waste, and iii) provide access to new chemical space. New chemical space contains molecular diversity with unknown potential. Current research focuses on i) enhancing chiral amine synthesis, ii) discovering salt-free coupling reactions, and iii) improving access to bromodomain inhibitors. These focus areas address specific longstanding synthetic challenges. The methods provide unique access to untapped chemical space, which researchers are exploring through collaboration for medicinal chemistry applications.
Professor Joseph Topczewski earned his bachelor's degree from the University of Wisconsin at Parkside, and his doctorate from the University of Iowa. He was a post-doctoral research at the University of Iowa and Michigan before joining the Department of Chemistry at the University of Minnesota in 2015.