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Steve Goldup

Prof. Stephen Goldup

School of Chemistry
University of Birmingham

11:00 - 12:00,
Mon 15 May, 2023


Prof. Goldup joins as an invited guest.

This is a departmental lecture for all students and staff. Please come along. Tea, coffee and refreshments will be provided from 10:45 on the Science Concourse.

Mechanically Chiral Molecules: Synthesis and Applications

Interlocked molecules can display forms of stereochemistry that do not rely on classical covalent stereogenic units, including many examples that have yet to be realised in chemical form.1 We have pioneered the use of a “small” macrocycle2,3 mediated active template4 reaction in combination with covalent chiral auxiliaries in order to allow the synthesis of mechanically planar chiral rotaxanes5,6,7 and chiral catenanes (Figure 1),8 as well as discovering new forms of mechanical stereochemistry.9 In this lecture I will describe our recent efforts to improve access to these intriguing molecules, and their applications in enantioselective sensing and catalysis.10

Schematic representation of our auxiliary approach to a topologically chiral catenane


Steve obtained an MChem degree from the University of Oxford where he began his research career with a Part II project in the group of Sir Prof. Jack Baldwin. He continued his research training with a PhD in natural product synthesis under the supervision of Prof. Tony Barrett before shifting focus to apply his synthetic skills to the realisation of mechanically interlocked non-natural products during post doctoral work with Prof. David Leigh at the University of Edinburgh where in 2007 he was appointed as Fixed Term Lecturer in Organic Chemistry. In 2008 he moved to Queen Mary with the award of a Leverhulme Trust Early Career Fellowship and in October 2009 he was awarded a Royal Society University Research Fellowship. In October 2014 the group moved to the University of Southampton where Steve took up the position of Associate Professor. In August 2017, Steve was promoted to Professor of Chemistry and in 2019 was awarded a Royal Society Wolfson Research Fellowship. Research in the Goldup Group focusses on the synthesis of novel mechanically interlocked molecules and their application as sensors, catalysts and materials.


1 E. M. G. Jamieson, F. Modicom, S. M. Goldup, Chirality in Rotaxanes and Catenanes, Chem. Soc. Rev. 2018, 47, 5266-5311.

2 H. Lahlali, K. Jobe, M. Watkinson, S. M. Goldup, Macrocycle Size Matters: "Small" Functionalized Rotaxanes in Excellent Yield Using the Cuaac Active Template Approach, Angew. Chem. Int. Ed. 2011, 50, 4151-4155.

3 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.

4 M. Denis, S. M. Goldup, The Active Template Approach to Interlocked Molecules, Nat Rev Chem 2017, 1, 0061.

5 R. J. Bordoli, S. M. Goldup, An Efficient Approach to Mechanically Planar Chiral Rotaxanes, J. Am. Chem. Soc. 2014, 136, 4817-4820.

6 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.

7 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.

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 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.

10 A. W. Heard, S. M. Goldup, Synthesis of a Mechanically Planar Chiral Rotaxane Ligand for Enantioselective Catalysis, Chem 2020, 6, 994-1006.