Functionalized heterocycles have played an increasingly important role in the development of novel pharmaceutical compounds.  Aziridinones are of great interest due to their highly strained 3-membered heterocyclic ring structure. Based on the strength of the nucleophile, aziridinones can ring open at the C-2 and C-3 position to give a library of potential products. In 1984, Howard Alper converted aziridinones into azetidine-2,4-diones using rhodium and cobalt complexes providing the first example of metal insertion into these compounds, but the 3-membered heterocycles ring opening chemistry has yet to be explored.  We believed that by inserting a metal into these aziridinones, the complexes formed could perform further chemistry with highly functionalized compounds.  We have developed a new transition metal-catalyzed process for the N-functionilization of a variety of heterocyclic precursors.  The benefit of the developed method is that complex heterocycles may be synthesized from strained heterocyclic precursors under mild reaction conditions in 25 minutes.

Synthesis of complex heterocycles via novel transition metal-catalyzed reactions

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.