Asymmetric Suzuki reactions and an organic supramolecular oscillator
Stephen Fletcher
Professor, Department of Chemistry
University of Oxford
Monday, October 21, 2024
11 a.m.
In-person and MS Teams
Abstract:ÌýThe Suzuki-Miyaura reaction is so important to medicinal chemistry that it has skewed new medicines toward flat molecules – possibly to the detriment of human health.1ÌýIt 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 group has developed a series of catalytic asymmetric C(sp3)-C(sp3) and C(sp3)-C(sp2) cross-couplings reactions2Ìýbased 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. Here I will discuss recently developed extensions of these methods to (i) substrates where more than one stereogenic centre is controlled in a single transformation, (ii) where regiochemistry is be controlled using chelation in non-pseudosymmetrical starting materials, and (iii) the synthesis of biologically active compounds. I will also discuss how we developed an autonomously oscillating supramolecular system3Ìýfrom autocatalytic self-reproducing lipids originally explored to better understand how life may have spontaneously emerged on Earth.4
References:
1³¢´Ç±¹±ð°ù¾±²Ô²µÌýet al, J. Med. Chem.Ìý2009, 52, 6756.
2H. YouÌýet al, NatureÌý2015, 517, 351; M. SideraÌýet al, Nature Chem.Ìý2015, 7, 935; S. WebsterÌýet al, Aldirchimica ActaÌý2024, 3.
3M. HowlettÌýet al, Nature Chem.Ìý2022, 14, 805.
4M. HowlettÌýet al, Nature Rev. Chem.Ìý2023, 7, 673.