Events

Date: 30 October 2024   Time: 14:00 - 15:00

Location: GO Jones LT

Catalyst Control in Complex Molecule Synthesis
Darren J. Dixon
Department of Chemistry, University of Oxford, Oxford, United Kingdom
e-mail: Darren.dixon@chem.ox.ac.uk

In this presentation, new "synthesis inspired" user-friendly broad scope catalytic strategies for
forging the key carbon-carbon bonds of late-stage synthetic intermediates en route to various complex
alkaloid natural products will be described. In one strand, the use of the abundant and venerable tertiary amide as a precursor to reactive enamine and dienamine intermediates via reductive activation will be explored as a new approach to aspidosperma and vinca alkaloids. In addition, the strategic use of the iridium catalyzed reductive activation of tertiary amides and lactams for downstream coupling to a host of nucleophilic reagents for the synthesis of alpha branched tertiary amines will be described.

The lecture will finish with a computational and experimental exploration of the mechanism of the
reductive activation step, as well as the key active catalytic species, the understanding of which explains the exquisite chemoselectivity of the reaction but has also allowed for the development of much more highly active catalytic systems that can hydrosilylate a broader range of functional groups, paving the way to yet more synthetic developments and applications.

References
1. D. Matheau-Raven and D. J. Dixon Angew. Chem. Int. Ed. Angew. Chem. Int. Ed. 2021, 60, 19725.
2. D. Matheau-Raven, E. Boulter, T. Rogova and D. J. Dixon Org. Lett. 2021, 23, 8209.
3. D. Matheau-Raven and D. J. Dixon J. Org. Chem. 2022, 87, 12498.
4. P. Biallas, K. Yamazaki and D. J. Dixon Org. Lett. 2022, 24, 2002.
5. B. Pijper, R. Martín, A. J. Huertas-Alonso, M. L. Linares, E. López, J. Llaveria, Á. Díaz-Ortiz, D. J. Dixon,
A. de la Hoz and J. Alcázar, Org. Lett., 2024, 26, 2724.
6. B. D. A. Shennan, S. Sánchez Alonso, G. Rossini and D. J. Dixon J. Am. Chem. Soc. 2023, 145, 21745.

Speaker Biography: Professor Darren J. Dixon studied Chemistry at the University of Oxford, where he received his Master's degree in 1993, and his DPhil in 1997 for work supervised by Prof Stephen G. Davies. After postdoctoral work with Professor Steven V. Ley CBE FRS, he joined the faculty at the Department of Chemistry in Cambridge in 2000. In 2004 he took a Senior Lecturership at The University of Manchester and in 2007 he was promoted to Reader. In 2008 he moved to his current post at the University of Oxford where he is Professor of Chemistry and is the Knowles-Williams Fellow in Organic Chemistry at Wadham College. His research programme is centred on catalysis and synthetic organic chemistry, and focuses on the development of new catalyst-enabled (enantioselective) synthetic
methodologies and their application in complex molecule synthesis. He is the recipient of various awards including the Royal Society of Chemistry's Catalysis in Organic Chemistry Award, the 2023 Tilden Prize and the 2024 Charles Rees Award.