About the Seminar:

Amines are fundamental chemical motifs commonly found in molecules of importance to chemistry, biology and medicine. Their Lewis basic properties arising from the lone pair of electrons makes them ideal as ligands for transition metal catalysts and organometallic complexes. In nature they are often found contained within alkaloid secondary metabolites produced by organisms such as bacteria, fungi, and plants. Many of these possess important pharmacological activities some of which are exploited currently in the clinic. With such widespread utility and application, new strategic approaches for their synthesis allowing effective, reliable and broad-scope access would have far-reaching impact across synthetic chemistry and into the biomedical sciences.

In this presentation, new, user-friendly broad scope reductive and oxidative strategies using abundant nitrogen containing monomer sets – including amides, primary amines and imines – as substrates for carbon-carbon bond formation will be described. The presentation will include details of the new synthetic methodologies as well as their provenance and applications on complex natural product total synthesis. ^[1-5]

References:

1. “Iridium-catalyzed reductive Ugi-type reactions of tertiary amides” Xie, L.; Dixon, D. J. Sci. 2017, 8, 7492.
2. “Photocatalytic Three-Component Umpolung Synthesis of 1,3-Diamines”, T. Rossolini, J. A. Leitch, R. Grainger, D. J. Dixon, Lett. 2018, 20, 6794.
3. “Photocatalytic reverse polarity Povarov reaction” A. Leitch, A. L. Fuentes de Arriba, J. Tan, O. Hoff, C. M. Martinez, D. J. Dixon Chem. Sci. 2018, 9, 6653.
4. “Primary α-Tertiary Amine Synthesis via α-C–H Functionalization”, D. Vasu, A. L. Fuentes de Arriba, J. Leitch, A. de Gombert and D. J. Dixon, Sci. 2019, 10, 3401.
5. “Iridium-Catalyzed Aza-Spirocyclisation of Indole-Tethered Amides: an Interrupted Pictet-Spengler Reaction Gabriel, A. Gregory, D. J. Dixon, Org. Lett. 2019, 21, 6658.
6. “General α-Amino 1,3,4-Oxadiazole Synthesis via Late-Stage Reductive Functionalization of Tertiary Amides and Lactams”, D. Matheau-Raven and D. J. Dixon Chem. Int. Ed. 2021, DOI: 10.1002/anie.202107536
7. “General Pyrrolidine Synthesis via Iridium-Catalyzed Reductive Azomethine Ylide Generation from Tertiary Amides & Lactams”, K. Yamazaki, P. Gabriel, G. Di Carmine, J. Pedroni, M. Farizyan, T. A. Hamlin and D. J. Dixon ACS Catal. 2021, 11, 7489.

About the Speaker:

Darren J. Dixon is Professor of Chemistry at the University of Oxford. He obtained his BA, MA and D. Phil (supervised by Professor Stephen Davies) from the University of Oxford. After a postdoctoral fellowship with Professor Steve Ley FRS he was appointed to the Staff of the Department of Chemistry, University of Cambridge in 2000. In 2004 he took a Senior Lectureship at The University of Manchester and was promoted to Reader in 2007. In 2008, he moved to his current position at Oxford where he is also the Knowles-Williams Tutorial Fellow in Organic Chemistry at Wadham College. His research is centred on the development of new catalyst-enabled synthetic methodologies and their application to the synthesis of structurally complex scaffolds, natural products and molecules of biological significance. His honors include an EPSRC Leadership Fellowship, the RSC Catalysis in Organic Chemistry Award, the AstraZeneca Research Award, Novartis Lectureship, Swiss Chemical Society Lectureship.

http://dixon.chem.ox.ac.uk/