Selective formation of γ-lactams via C-H amidation enabled by tailored iridium catalysts
- Journal:
- Science
- Published:
- DOI:
- 10.1126/science.aap7503
- Affiliations:
- 2
- Authors:
- 6
Research Highlight
Iridium catalyst puts a lactam ring on it
© molekuul_be/Shutterstock
Cyclic, nitrogen-containing structures called lactams are well known for their medicinal properties. A whole family of antibiotics is based on four-membered lactam rings. The five-membered lactam ring, however, is notoriously hard to synthesise. Now, guided by density functional theory, KAIST researchers have developed a catalyst that can selectively deliver these sought-after structures.
The challenge with forming catalytic five-membered lactam structures has been a competing reaction pathway. When the catalyst binds to the nitrogen-containing lactam precursor, this reactive intermediate typically decomposes to form a linear structure called an isocyanate rather than cyclizing to give the desired lactam.
After studying this competing reaction pathway in detail, the KAIST team designed a set of iridium catalysts that highly favour lactam formation over isocyanate formation. The catalysts were able to incorporate five-membered lactam rings into a wide range of molecules of potential medical interest.
References
- Science 359, 1016–1021 (2018). doi: 10.1126/science.aap7503
Institutions | Authors | Share |
---|---|---|
Korea Advanced Institute of Science and Technology (KAIST), South Korea | 0.50 | |
Center for Catalytic Hydrocarbon Functionalizations, IBS, South Korea | 0.50 |