Home Beyond Macrocycles: Bond Disconnections Enabled by Olefin Metathesis
2023

Beyond Macrocycles: Bond Disconnections Enabled by Olefin Metathesis

by cyb2025
P. Wheeler
Alkene Metathesis
Heterocycle synthesis
olefin metathesis
Peer Reviewed
Retrosynthesis
Ring-closing metathesis

PHILIP WHEELER
Umicore Precious Metals Chemistry

ABSTRACT

Olefin metathesis is a powerful tool that enables unique bond disconnection strategies via carbon-carbon bonds. It has been employed in commercial scale synthesis across multiple industries and in multiple reaction types including ring-closing, cross, and ring-opening metathesis. Among these, macrocyclization by ring-closing metathesis stands out as a hallmark of the technology. However, ring-closing metathesis can also serve as a highly efficient entry to smaller rings. In this article, we highlight retrosynthetic strategies toward 5- and 6-membered nitrogen heterocycles, including in the context of a commercial drug manufacturing process.

In the fifty years from its discovery to the 2005 Nobel Prize awarded to Yves Chauvin, Richard Schrock, and Robert Grubbs, olefin metathesis evolved from a curious oddity to a reliable tool for chemical synthesis and polymerization. These advances were made possible by tireless investigation of mechanism, (1) the development of well-defined catalysts, (2) and the exploration of those catalysts with a multitude of potential substrates (3).

 

Since 2005, this work has blossomed into new commercial applications in materials science,(4) biorenewable chemistry, (5) and pharmaceuticals (6).
Now, another generation of commercial-scale applications are currently in development, from pheromones for crop protection (7) to tough materials for 3D-printing (8) to structural paints for automotive coating (9).

 

ABOUT THE AUTHOR

Philip Wheeler is a native of California and earned a B. A. in chemistry at UC Santa Cruz in 2004. He worked at Amgen in Thousand Oaks as an associate in process chemistry before starting his Ph. D. studies in 2007 at Colorado State University in the laboratory of Tom Rovis. After completing his Ph. D. in 2013, Philip joined Sigma Aldrich in Milwaukee as a product manager for their catalysis portfolio. In 2015, he moved back to California to join Materia as a business development manager and joined Umicore in 2018 as part of their acquisition of Materia’s Grubbs Catalyst® Portfolio. Philip is enthusiastic about catalysis and connecting clients with the best solution for their process.

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