Mechanically Chiral Molecules: Synthesis and Applications
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Mechanically Chiral Molecules: Synthesis and Applications
Wed, 25/03/2026 - 14:00 to 15:00
Location:
Speaker:
Prof Steve Goldup
Affiliation:
University of Birmingham
Synopsis:
Interlocked molecules can display forms of stereochemistry that do not rely on classical covalent stereogenic units,1 including many examples that have yet to be realised in chemical form. We have pioneered the use of a “small” macrocycle2 mediated active template3 reaction in combination with covalent chiral auxiliaries to allow the synthesis of mechanically planar chiral rotaxanes4,5,6,7 and catenanes,8,9,10 as well as discovering new forms of mechanical stereochemistry.11,12,13 and explored their applications in enantioselective sensing and catalysis.14
1. S. M. Goldup, The End of the Beginning of Mechanical Stereochemistry, Acc. Chem. Res. 2024, 57, 1696-1708.
2. J. E. M. Lewis, R. J. Bordoli, M. Denis, C. J. Fletcher, M. Galli, E. A. Neal, E. M. Rochette, S. M. Goldup, High Yielding Synthesis of 2,2′-Bipyridine Macrocycles, Versatile Intermediates in the Synthesis of Rotaxanes, Chem. Sci. 2016, 7, 3154-3161.
3. M. Denis, S. M. Goldup, The Active Template Approach to Interlocked Molecules, Nat. Rev. Chem. 2017, 1, 0061.
4. R. J. Bordoli, S. M. Goldup, An Efficient Approach to Mechanically Planar Chiral Rotaxanes, J. Am. Chem. Soc. 2014, 136, 4817-4820.
5. M. A. Jinks, A. de Juan, M. Denis, C. J. Fletcher, M. Galli, E. M. G. Jamieson, F. Modicom, Z. Zhang, S. M. Goldup, Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes, Angew. Chem. Int. Ed. 2018, 57, 14806-14810.
6. A. de Juan, D. Lozano, A. W. Heard, M. A. Jinks, J. M. Suarez, G. J. Tizzard, S. M. Goldup, A Chiral Interlocking Auxiliary Strategy for the Synthesis of Mechanically Planar Chiral Rotaxanes, Nat. Chem. 2022, 14, 179-187.
7. S. Zhang, A. Rodríguez-Rubio, A. Saady, G. J. Tizzard, S. M. Goldup, A Chiral Macrocycle for the Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes and Catenanes, Chem 2023, 9, 1195-1207.
8. M. Denis, J. E. M. Lewis, F. Modicom, S. M. Goldup, An Auxiliary Approach for the Stereoselective Synthesis of Topologically Chiral Catenanes, Chem 2019, 5, 1512-1520.
9. A. Rodriguez-Rubio, A. Savoini, F. Modicom, P. Butler, S. M. Goldup, A Co-Conformationally "Topologically" Chiral Catenane, J. Am. Chem. Soc. 2022, 144, 11927-11932.
10. N. Pairault, F. Rizzi, D. Lozano, E. M. G. Jamieson, G. J. Tizzard, S. M. Goldup, A Catenane That Is Topologically Achiral Despite Being Composed of Oriented Rings, Nat. Chem. 2023, 15, 781-786.
11. J. R. J. Maynard, P. Gallagher, D. Lozano, P. Butler, S. M. Goldup, Mechanically Axially Chiral Catenanes and Noncanonical Mechanically Axially Chiral Rotaxanes, Nat. Chem. 2022, 14, 1038-1044. 12. P. R. Gallagher, A. Savoini, A. Saady, J. R. J. Maynard, P. V. W. Butler, G. J. Tizzard, S. M. Goldup, Facial Selectivity in Mechanical Bond Formation: Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle, J. Am. Chem. Soc. 2024, 146, 9134-9141.
13. A. Savoini, P. R. Gallagher, A. Saady, S. M. Goldup, The Final Stereogenic Unit of [2]Rotaxanes: Type 2 Geometric Isomers, J. Am. Chem. Soc. 2024, 146, 8472-8479.
14. A. W. Heard, S. M. Goldup, Synthesis of a Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis, Chem 2020, 6, 994-1006.
Biography:
Steve grew up in Gloucester where attended Sir Thomas Rich’s School. He studied for an MChem at the University of Oxford where he began his research career with a Part II project in the group of Sir Prof. Jack Baldwin. He then completed a PhD in natural product synthesis under the supervision of Prof. Tony Barrett, before shifting focus to apply his synthetic skills to mechanically interlocked non-natural products with Prof. David Leigh at the University of Edinburgh. In Edinburgh Steve began his formal teaching career as a Fixed Term Lecturer in Organic Chemistry.
In 2008, Steve moved to Queen Mary University of London with the award of a Leverhulme Trust Early Career Fellowship and in 2009 he was awarded a Royal Society University Research Fellowship. In 2014, Steve and his group moved to the University of Southampton, where he took up the position of Associate Professor. While in Southampton, Steve was promoted to Professor of Chemistry in 2017 and in 2019 was awarded a Wolfson Research Fellowship. In 2023, Steve and his team moved to the University of Birmingham where Steve is Chair of Chemistry and the Molecular Synthesis Section Lead.
Research in the Goldup group focusses on developing efficient methods to synthesise novel mechanically interlocked molecules, including examples displaying mechanical stereochemistry, to allow the practical benefits of the mechanical bond to be realised. The ultimate goal of research in the Goldup Group is that rotaxanes and catenanes become truly useful in medicine, catalysis, materials and beyond.
Steve has received several awards including: RSC Corday Morgan (2025), Finalist in the 2020 Blavatnik UK Young Scientist Prize (2020), RSC Macrocyclic and Supramolecular Chemistry Bob Hay Lectureship (2016), RSC Hickinbottom Award (2014), Gregynog Synthesis Meeting David Hill Cup (2012), Thieme Journal Chemistry Award (2012).
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