13:00 - 14:00
Weds 5 June 2024

PLT

Prof Stephen Fletcher will deliver his RSC 2023 Dalton Early Career Prize Lecture.

This is a departmental lecture for all students and staff. Please come along. Refreshments will be provided at 12:45 outside PLT

Additions to racemates: A strategy for developing asymmetric cross-coupling reactions

Stephen Fletcher
Department of Chemistry, University of Oxford
12 Mansfield Road, Oxford, OX1 3TA
Stephen.fletcher@chem.ox.ac.uk Link opens in a new window

Cross-coupling reactions of two sp2-hybridized carbon species are highly developed, and the Suzuki-Miyaura reaction is so important to medicinal chemistry that it has skewed drugs toward flat molecules, possibly to the detriment of human health.[1] It is widely understood that a 3-dimensional equivalent would be important and many groups around the world are developing cross-coupling reactions to make 3D molecules.

Our research group has developed a series of catalytic asymmetric C(sp3)-C(sp3) and C(sp3)-C(sp2) cross-couplings reactions[1] based on transition metal catalyzed asymmetric additions of non-stabilized organometallic nucleophiles to racemic starting materials. These processes convert both enantiomers of the starting material into a single enantiomerically enriched product while forming the new C–C bond.[3]

This talk will discuss recently developed extensions of these methods to substrates (i) where more than one stereogenic centre is controlled in a single transformation, (ii) where regiochemistry can be controlled using non-pseudosymmetrical starting materials, and (iii) the application of these methods to biologically active compounds.

References: (1) Lovering et al. J. Med. Chem. 2009, 52, 6756. (2) H. You et al, Nature 2015, 517, 351; M. Sidera et al. Nature Chem. 2015, 7, 935. (3) For mechanistic studies see: E. Rideau et al. J. Am. Chem. Soc. 2017, 39, 5614; L. van Dijk et al. Nature Cat. 2021, 4, 284.