Ian Fleming (chemist)

For other people named Ian Fleming, see Ian Fleming (disambiguation).

Ian Fleming FRS
Born	Ian Fleming (1935-08-04) 4 August 1935 (age 90) Staffordshire, England
Alma mater	Pembroke College, Cambridge
Spouse	Mary Bernard
Awards	Tilden Prize (1980)
Scientific career
Fields	Organic chemistry Organosilicon chemistry
Institutions	University of Cambridge
Thesis	(1962)
Doctoral advisor	John Harley-Mason

Ian Fleming (born 4 August 1935) is an English organic chemist, an emeritus professor of the University of Cambridge, and an emeritus fellow of Pembroke College, Cambridge. He was the first to determine the full structure of chlorophyll (in 1967) and was involved in the development of the synthesis of cyanocobalamin by Robert Burns Woodward. He has made major contributions to the use of organosilicon compounds for stereoselective syntheses; reactions which have found application in the synthesis of natural compounds. He is also a prolific author, and has written a number of textbooks, encyclopedia chapters and influential review articles.

Early life and education

Ian Fleming was born on 4 August 1935, in Kingswinford, Staffordshire and grew up in Stourbridge, Worcestershire, where he attended the King Edward VI Grammar School for Boys. He was accepted to study Natural Sciences at Pembroke College, Cambridge but first joined the Royal Corps of Signals to complete compulsory National Service, in 1954–1956. He was commissioned as a second lieutenant. ^[1]

He graduated with a B.A. in 1959 from the University of Cambridge and immediately started research in the Department of Chemistry, under the supervision of John Harley-Mason, studying decarboxylative elimination and the chemistry of enamines. He completed his Ph.D. in 1962. ^{[1] [2]}

Career

Fleming obtained a research fellowship at Pembroke College in 1962. In 1963–1964 he spent a post-doctoral year at Harvard University with R.B. Woodward working on the synthesis of vitamin B₁₂. He returned to Cambridge in autumn 1964 when appointed by Lord Todd as a University Demonstrator. ^[1] He was promoted and by 1986 was a Reader; in 1998 he became a Professor of Organic Chemistry. Throughout the period 1964–2002 he was a Fellow and Assistant Director of Studies in Natural Sciences at Pembroke College. He was obliged by the statutes of the University to retire in 2002 when he reached the age of 67. ^{[2] [3]}

Teaching

He has authored popular undergraduate textbooks on spectroscopic methods of structure determination, organic synthesis, and applications of frontier molecular orbital theory to problems in organic chemistry. ^[4] The book Spectroscopic Methods in Organic Chemistry, which he co-wrote with Dudley Williams, was first published in 1966 and had reached edition six and been translated into multiple languages by the time of Williams' death in 2010. ^[5] Fleming published a seventh edition in 2019, following his teaching a one-semester course on the subject at the University of Illinois for seven years from 2012-2018. ^[4] According to John Sulston, Fleming in the 1960s "was young, personable and really sparky about how things worked". ^[6]

As of 2024 ^[update] , although formally retired, Fleming continues to give a course of six lectures on organic spectroscopy to third-year undergraduates in the Cambridge Chemistry Department. ^[7]

Research

Red and green markers in ring D of chlorophyll a where absolute stereochemistry was established

In 1967, Fleming published a paper which provided the final details of the structure of chlorophyll a by confirming the absolute configuration of the two sidechains attached to one of the rings of the macrocycle. ^{[8] [9] [10]}

In 1971–1972, while on sabbatical at McGill University, Fleming worked on the synthesis of the highly stable 8-cycloheptatrienylheptafulvenyl carbocation. ^{[2] [11]} More significantly, during that period he developed ideas for applying silicon within organic chemistry. ^[12] This lead to advances in the topic of organosilicon chemistry for organic synthesis, especially for the stereoselective production of chiral molecules. ^[2]

His work on what is now called the Fleming–Tamao oxidation allows the replacement of a carbon-silicon bond with a carbon-oxygen bond in a reaction which is stereospecific with retention of configuration. This allows the silicon group to be used as a functional equivalent of the hydroxyl group. ^{[13] [14]} In the early method shown for the C-Si bond's replacement, two steps are required: treatment with fluoroboric acid followed by an oxidation using meta-chloroperoxybenzoic acid. A one-step procedure using potassium bromide and peracetic acid in acetic acid has also been described. ^[15]

He has over 200 scientific publications, including major contributions to the chemical encyclopedia "Comprehensive Organic Chemistry", and many influential review articles. ^[16]

His later work, building on the application of silicon in organic chemistry he had developed, included the synthesis of the natural products thienamycin, ^{[17] [18]} nonactin, ^{[19] [20]} and sparteine. ^{[21] [22]}

Selected publications

• Fleming, Ian; Woodward, R. B. (1973). "A synthesis of (–)-(R)-trans-β-(1,2,3-trimethylcyclopent-2-enyl)acrylic acid". J. Chem. Soc., Perkin Trans. 1: 1653–1657. doi:10.1039/P19730001653.
• Fleming, Ian (1979). "13: Organic Silicon Chemistry". In Barton, D. H. R.; Ollis, W. D. (eds.). Comprehensive Organic Chemistry. Vol. 3. Oxford: Pergamon. pp. 541–686.
• Fleming, Ian; Dunoguès, Jacques; Smithers, Roger (1989). "The Electrophilic Substitution of Allylsilanes and Vinylsilanes". Organic Reactions. Wiley. pp. 57–575. doi:10.1002/0471264180.or037.02. ISBN   978-0-471-26418-7.
• Fleming, Ian; Barbero, Asuncion; Walter, David (1997). "Stereochemical Control in Organic Synthesis Using Silicon-Containing Compounds". Chemical Reviews. 97 (6): 2063–2192. doi:10.1021/cr941074u. PMID   11848898.
• Fleming, Ian (Spring 2009). "Half a century in Lensfield Road: Ian Fleming on the people" (PDF). chem@cam (39): 11–12. Retrieved 29 September 2025.
• Fleming, Ian (August 2011). Molecular Orbitals and Organic Chemical Reactions: student edition. Wiley. p. 376. ISBN   978-0-470-74659-2.
• Fleming, Ian (August 2011). Molecular Orbitals and Organic Chemical Reactions: reference edition. Wiley. p. 528. ISBN   978-1-119-96467-4.
• Fleming, Ian (2015). Pericyclic Reactions (2 ed.). Oxford University Press. p. 118. ISBN   978-0-19-968090-0. ^[23]
• Fleming, Ian; Williams, Dudley (2019). Spectroscopic Methods in Organic Chemistry (7 ed.). Springer International Publishing. p. 432. ISBN   978-3-030-18251-9.

Awards and prizes

• 1980 Tilden Prize of the Royal Society of Chemistry ^{[24] [25]}
• 1983 RSC Prize for Organic Synthesis
• 1993 Elected a Fellow of the Royal Society ^[26]

Personal life

Fleming married Mary Bernard, an author, in 1965; ^[27] they have no children. ^[3] His interests include photography and he has taken portraits of every Pembroke College Fellow since 1963. ^[28] Some of his work is included in the 2025 book which describes the buildings and gardens of the College. ^[29] Fleming has been credited as being one of those who actively campaigned for the admission of women to Pembroke. ^[30]

References

1. Fleming, Ian. "School and University Studies". Archived from the original on 3 June 2023. Retrieved 1 October 2025.
2. Simke, Leah (29 August 2015). "Chemists with Named Oxidations" (PDF). baranlab.org. Retrieved 29 September 2025.
3. Fleming, Ian. "Academic posts". Archived from the original on 3 June 2023. Retrieved 1 October 2025.
4. See selected publications
5. Sanders, Jeremy K. M.; Robinson, Dame Carol V. (31 December 2017). "Dudley Howard Williams. 25 May 1937 — 3 November 2010". Biographical Memoirs of Fellows of the Royal Society. 63: 567–583. doi: 10.1098/rsbm.2017.0009 .
6. Sulston, John (Winter 2017). "Q&A John Sulston" (PDF). chem@cam (56): 4. Retrieved 1 October 2025.
7. "Part II Chemistry: A Guide to the Course" (PDF). teaching.ch.cam.ac.uk. 2024. p. 30. Retrieved 1 October 2025.
8. Fleming, IAN (1967). "Absolute Configuration and the Structure of Chlorophyll". Nature. 216 (5111): 151–152. Bibcode:1967Natur.216..151F. doi:10.1038/216151a0.
9. Senge, Mathias; Ryan, Aoife; Letchford, Kristie; MacGowan, Stuart; Mielke, Tamara (2014). "Chlorophylls, Symmetry, Chirality, and Photosynthesis". Symmetry. 6 (3): 788. Bibcode:2014Symm....6..781S. doi: 10.3390/sym6030781 .
10. Scheer, Hugo (2 December 2012). "1 Synthesis and Stereochemistry of Hydroporphyrins". In Dolphin, David (ed.). The Porphyrins V2. New York: Elsevier. pp. 24–25. ISBN   978-0-323-14956-3.
11. Fleming, Ian (1973). "Synthesis of the 8-cycloheptatrienylheptafulvenyl cation". Journal of the Chemical Society, Perkin Transactions 1: 1019. doi:10.1039/P19730001019.
12. Fleming, Ian. "Independent research". Archived from the original on 27 April 2025. Retrieved 1 October 2025.
13. Jones, Graeme R.; Landais, Yannick (1996). "The oxidation of the carbon-silicon bond". Tetrahedron. 52 (22): 7599–7662. doi:10.1016/S0040-4020(96)00038-5.
14. Barrett, Anthony G. M.; Head, John; Smith, Marie L.; Stock, Nicholas S.; White, A. J. P.; Williams, D. J. (1999). "Fleming−Tamao Oxidation and Masked Hydroxyl Functionality: Total Synthesis of (+)-Pramanicin and Structural Elucidation of the Antifungal Natural Product (−)-Pramanicin". The Journal of Organic Chemistry. 64 (16): 6005–6018. doi:10.1021/jo9905672.
15. Fleming, Ian; Henning, Rolf; Parker, David C.; Plaut, Howard E.; Sanderson, Philip E. J. (1995). "The phenyldimethylsilyl group as a masked hydroxy group". Journal of the Chemical Society, Perkin Transactions 1 (4): 317–337. doi:10.1039/p19950000317. ISSN   0300-922X.
16. "Fleming, Ian". scopus.com. Elsevier. Retrieved 30 September 2025.
17. Fleming, Ian; Kilburn, Jeremy D. (1998). "Stereocontrol in organic synthesis using silicon-containing compounds. A formal synthesis of (±)-thienamycin". Journal of the Chemical Society, Perkin Transactions 1 (17): 2663–2672. doi:10.1039/A804271C.
18. Breunig, Jamie L.; Lin, You-Chen; Pierce, Joshua G. (2024). "An enantioselective formal synthesis of thienamycin". Tetrahedron Letters. 144 155132. doi:10.1016/j.tetlet.2024.155132. PMC   11242926 . PMID   39006392.
19. Fleming, Ian; Ghosh, Sunil K. (1998). "Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of nonactin". Journal of the Chemical Society, Perkin Transactions 1 (17): 2733–2748. doi:10.1039/A804284E.
20. Gustafson, Afton; Kahr, Bart (2024). "Optical Activity of Nonactin and Its Cation Complexes". Chirality. 36 (8) e23703. doi:10.1002/chir.23703. PMID   39034362.
21. Buttler, Thomas; Fleming, Ian; Gonsior, Sabine; Kim, Bo-Hye; Sung, A.-Young; Woo, Hee-Gweon (2005). "A synthesis of (±)-sparteine". Org. Biomol. Chem. 3 (8): 1557–1567. doi: 10.1039/B502213D . PMID   15827657.
22. Firth, James D.; Canipa, Steven J.; Ferris, Leigh; O'Brien, Peter (2018). "Gram-Scale Synthesis of the (−)-Sparteine Surrogate and (−)-Sparteine" (PDF). Angewandte Chemie International Edition. 57 (1): 223–226. doi:10.1002/anie.201710261. PMID   29155468.
23. Rzepa, Henry (8 September 2015). "[Review of] Pericyclic reactions". chemistryworld.com.
24. "RSC Tilden Prize Previous Winners". Royal Society of Chemistry. Archived from the original on 5 August 2018. Retrieved 29 September 2025.
25. Fleming, Ian (1981). "Tilden Lecture. Some uses of silicon compounds in organic synthesis". Chemical Society Reviews. 10: 83. doi:10.1039/CS9811000083.
26. "Professor Ian Fleming FRS". royalsociety.org. 2025. Retrieved 29 September 2025.
27. Muise, Jackie (12 September 2015). "George Frederick Clarke makes a comeback". Telegraph-Journal . New Brunswick. p. F4. ISSN   0837-3736 – via newspapers.com.
28. "Portraits of Women Fellows in the Hall". pem.cam.ac.uk. May 2014. Retrieved 2 October 2025.
29. Smith, Chris, ed. (2025). Pembroke College, Cambridge: The Buildings and Gardens. p. 159. ISBN   9781785515330.
30. Morris, Nami (March 2025). "March 2025 - Nami Morris, Deputy Development Director". pem.cam.ac.uk. Retrieved 2 October 2025.

External links

• Biographical note, Chemistry Department Lectures, The University of Illinois at Urbana-Champaign
• Archive of Fleming's website at the Internet Archive in August 2024
• Short cuts on YouTube. Fleming lecture to Cambridge SciSoc, 20 November 2023