David MacMillan

Last updated

Professor
Sir David MacMillan
FRS FRSE
David MacMillan.jpg
MacMillan in 2021
Born
David William Cross MacMillan

(1968-03-16) 16 March 1968 (age 56)
Bellshill, Scotland, United Kingdom
CitizenshipUnited Kingdom
United States [1]
EducationBellshill Academy
Alma mater University of Glasgow (BSc)
University of California, Irvine (MSc, PhD)
Awards Corday-Morgan medal
Member of the National Academy of Sciences (2018)
Nobel Prize in Chemistry (2021)
Scientific career
Institutions
Thesis Stereocontrolled formation of bicyclic tetrahydrofurans and Enantioselective total synthesis of eunicellin diterpenes  (1996)
Doctoral advisor Larry E. Overman
Other academic advisorsErnest W. Colvin
David A. Evans
Doctoral students Vy Dong, Tehshik Yoon, Robert R. Knowles

Sir David William Cross MacMillan (born 16 March 1968) [2] is a Scottish [8] chemist and the James S. McDonnell Distinguished University Professor of Chemistry at Princeton University, where he was also the chair of the Department of Chemistry from 2010 to 2015. [9] [10] He shared the 2021 Nobel Prize in Chemistry with Benjamin List "for the development of asymmetric organocatalysis". [11] MacMillan used his share of the $1.14 million prize to establish the May and Billy MacMillan Foundation. [12]

Contents

Education and early life

MacMillan was born in Bellshill, North Lanarkshire, Scotland, in 1968 and grew up in nearby New Stevenston. [13] He attended the local state-funded schools, New Stevenston Primary and Bellshill Academy, and credited his Scottish education and Scottish upbringing for his success. [14] [13]

He received his undergraduate degree in chemistry at the University of Glasgow, where he worked with Ernie Colvin. [15] [16]

In 1990, he left the UK to begin his doctoral studies under the direction of Professor Larry Overman at the University of California, Irvine. During this time, he focused on the development of new reaction methodology directed toward the stereocontrolled formation of bicyclic tetrahydrofurans. MacMillan's graduate studies culminated in the total synthesis of 7-(−)-deacetoxyalcyonin acetate, a eunicellin diterpenoid isolated from the soft coral Eunicella stricta. [17] He earned his Ph.D. in 1996. [16]

Career and research

Upon receiving his Ph.D., MacMillan accepted a postdoctoral position with Professor David Evans at Harvard University. His postdoctoral studies centered on enantioselective catalysis, in particular, the design and development of Sn(II)-derived bisoxazoline complexes (Sn(II)box). [16]

MacMillan began his independent research career as a member of the chemistry faculty at the University of California, Berkeley in July 1998. He joined the department of chemistry at Caltech in June 2000, where his group's research interests centered on new approaches to enantioselective catalysis. In 2004, he was appointed as the Earle C. Anthony Professor of Chemistry. He became the James S. McDonnell Distinguished University Professor at Princeton University in September 2006. [16]

First generation MacMillan catalyst MacMillan-Catalyst first generation.svg
First generation MacMillan catalyst

He is considered to be one of the founders of organocatalysis. [18] In 2000, MacMillan designed small organic molecules that can provide or accept electrons and therefore efficiently catalyse reactions. [18] [19] He developed catalysts that can drive asymmetric catalysis, in which a reaction produces more of the left-handed version of a molecule than the right-handed one (chirality), or vice versa. [18] MacMillan's research group has made many advances in the field of asymmetric organocatalysis, and they have applied these new methods to the synthesis of a range of complex natural products. [16] [18] He developed chiral imidazolidinone catalysts. [20] [19] [21] MacMillan catalysts  [ de ] are used in various asymmetric syntheses. Examples include Diels-Alder reactions, [19] 1,3-dipolar cycloadditions, [22] Friedel-Crafts alkylations [23] or Michael additions. [21]

MacMillan has also extensively developed photoredox catalysis for use in organic synthesis. [24] [25] [26]

Between 2010 and 2014, MacMillan was the founding editor-in-chief of the journal Chemical Science , the flagship general chemistry journal published by the Royal Society of Chemistry. [16]

As of March 2024, MacMillan has an h-index of 125 according to Google Scholar [27] and of 115 according to Scopus. [28]

Visit to Brasil

In April 2024, David MacMillan was in Brazil for events at the State University of Rio de Janeiro and the University of São Paulo. [29] In Rio, MacMillan asked to visit the headquarters of General Severiano, from Botafogo, and was received by the Club's board of directors. [30] Later in São Paulo, MacMillan held a short panel at University of São Paulo Chemistry Institute (IQ-USP) about his history as a researcher and recent Nobel laureate. In September 2024, he will attend the Brazilian Meeting on Organic Synthesis in Bento Gonçalves, Rio Grande do Sul, as opening lecture.

Honours and awards

MacMillan was knighted in the 2022 Birthday Honours for services to chemistry and science. [31] [32]

List

Related Research Articles

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<span class="mw-page-title-main">Enantioselective synthesis</span> Chemical reaction(s) which favor one chiral isomer over another

Enantioselective synthesis, also called asymmetric synthesis, is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric products in unequal amounts."

In chemistry, transfer hydrogenation is a chemical reaction involving the addition of hydrogen to a compound from a source other than molecular H2. It is applied in laboratory and industrial organic synthesis to saturate organic compounds and reduce ketones to alcohols, and imines to amines. It avoids the need for high-pressure molecular H2 used in conventional hydrogenation. Transfer hydrogenation usually occurs at mild temperature and pressure conditions using organic or organometallic catalysts, many of which are chiral, allowing efficient asymmetric synthesis. It uses hydrogen donor compounds such as formic acid, isopropanol or dihydroanthracene, dehydrogenating them to CO2, acetone, or anthracene respectively. Often, the donor molecules also function as solvents for the reaction. A large scale application of transfer hydrogenation is coal liquefaction using "donor solvents" such as tetralin.

<span class="mw-page-title-main">Organocatalysis</span> Method in organic chemistry

In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds. Because of their similarity in composition and description, they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved.

The Hajos–Parrish–Eder–Sauer–Wiechert and Barbas-List reactions in organic chemistry are a family of proline-catalysed asymmetric aldol reactions.

Within the area of organocatalysis, (thio)urea organocatalysis describes the use of ureas and thioureas to accelerate and stereochemically alter organic transformations. The effects arise through hydrogen-bonding interactions between the substrate and the (thio)urea. Unlike classical catalysts, these organocatalysts interact by non-covalent interactions, especially hydrogen bonding. The scope of these small-molecule H-bond donors termed (thio)urea organocatalysis covers both non-stereoselective and stereoselective reactions.

<span class="mw-page-title-main">Zoltan Hajos</span> Hungarian organic chemist (1926–2022)

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Proline organocatalysis is the use of proline as an organocatalyst in organic chemistry. This theme is often considered the starting point for the area of organocatalysis, even though early discoveries went unappreciated. Modifications, such as MacMillan’s catalyst and Jorgensen's catalysts, proceed with excellent stereocontrol.

<span class="mw-page-title-main">Photoredox catalysis</span>

Photoredox catalysis is a branch of photochemistry that uses single-electron transfer. Photoredox catalysts are generally drawn from three classes of materials: transition-metal complexes, organic dyes, and semiconductors. While organic photoredox catalysts were dominant throughout the 1990s and early 2000s, soluble transition-metal complexes are more commonly used today.

Frank Klaus Glorius is a German chemist and W3-Professor of organic chemistry in the Department of Chemistry and Pharmacy at the University of Münster.

<span class="mw-page-title-main">Scott E. Denmark</span> American chemist

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Tehshik Peter Yoon is a Canadian-born chemist who studies the new reaction methods for organic synthesis with the use of catalysis. Yoon currently is a professor at the University of Wisconsin–Madison in the chemistry department. For his contributions to science, he has received numerous awards including the Beckman Young Investigator Award and National Science Foundation CAREER Award.

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<span class="mw-page-title-main">Vy Maria Dong</span> American chemist

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Eric Meggers is a German chemist and professor of organic chemistry and chemical biology at the University of Marburg, Germany. His research currently focuses on the design of chiral catalysts for stereoselective synthesis.

<span class="mw-page-title-main">Nitro-Mannich reaction</span> Chemical reaction

The nitro-Mannich reaction is the nucleophilic addition of a nitroalkane to an imine, resulting in the formation of a beta-nitroamine. With the reaction involving the addition of an acidic carbon nucleophile to a carbon-heteroatom double bond, the nitro-Mannich reaction is related to some of the most fundamental carbon-carbon bond forming reactions in organic chemistry, including the aldol reaction, Henry reaction and Mannich reaction.

<span class="mw-page-title-main">Benjamin List</span> German chemist (born 1968)

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References

  1. 1 2 "Princeton's David MacMillan receives Nobel Prize in chemistry". Princeton University. 6 October 2021. Retrieved 7 October 2021.
  2. ↑ "David W.C. MacMillan". Nobel Foundation . Retrieved 23 January 2024.
  3. ↑ "David MacMillan: 'Being Scottish helped me win Nobel Prize'". BBC News. 7 October 2021. Retrieved 15 October 2021.
  4. ↑ Paterson, Laura (6 October 2021). "Scottish scientist jointly wins Nobel Prize in chemistry". www.standard.co.uk. Retrieved 8 October 2021.
  5. ↑ "Chemistry Nobel awarded for mirror-image molecules". BBC News. 6 October 2021. Retrieved 8 October 2021.
  6. ↑ Russell, Jennifer (6 October 2021). "Scots scientist wins Nobel Prize for chemistry". Daily Record. Retrieved 8 October 2021.
  7. ↑ "Scottish scientist jointly wins Nobel Prize in chemistry". uk.news.yahoo.com. 6 October 2021. Retrieved 8 October 2021.
  8. ↑ [1] [3] [4] [5] [6] [7]
  9. ↑ "The MacMillan Group". Macmillan Group. Archived from the original on 21 July 2020. Retrieved 15 June 2020.
  10. ↑ "David MacMillan". American Chemical Society Division of Organic Chemistry. 15 December 2016. Retrieved 12 July 2022.
  11. 1 2 "The Nobel Prize in Chemistry 2021". NobelPrize.org. Retrieved 6 October 2021.
  12. ↑ Service, Purdue News (23 January 2023). "David MacMillan, the 2021 Nobel laureate in chemistry, to join President Chiang for Presidential Lecture Series on Feb. 13". www.purdue.edu. Retrieved 16 August 2023.
  13. 1 2 "David MacMillan: 'Being Scottish helped me win Nobel Prize'". BBC News. 7 October 2021. Retrieved 7 October 2021.
  14. ↑ "Success wouldn't have happened if I wasn't Scottish, says Bellshill-born Nobel Prize winner". HeraldScotland. 7 October 2021. Retrieved 9 November 2021.
  15. ↑ "Bellshill man and former Glasgow University student David WC MacMillan wins the Nobel prize for chemistry". Glasgow Times. Retrieved 7 October 2021.
  16. 1 2 3 4 5 6 7 "David MacMillan". National Academy of Sciences . Retrieved 7 October 2021.
  17. ↑ MacMillan, David William Cross (1996). Stereocontrolled formation of bicyclic tetrahydrofurans; and, Enantioselective total synthesis of eunicellin diterpenes (Ph.D. thesis). University of California, Irvine. OCLC   35966904. ProQuest   304225710.
  18. 1 2 3 4 Castelvecchi, Davide; Stoye, Emma (6 October 2021). "'Elegant' catalysts that tell left from right scoop chemistry Nobel". Nature. 598 (7880). Springer Science and Business Media LLC: 247–248. Bibcode:2021Natur.598..247C. doi: 10.1038/d41586-021-02704-2 . ISSN   0028-0836. PMID   34616090. S2CID   238422185.
  19. 1 2 3 Ahrendt, Kateri A.; Borths, Christopher J.; MacMillan, David W. C. (15 April 2000). "New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction". Journal of the American Chemical Society. 122 (17). American Chemical Society (ACS): 4243–4244. doi:10.1021/ja000092s. ISSN   0002-7863.
  20. ↑ "David MacMillan". Princeton University Department of Chemistry. 21 July 2014. Archived from the original on 7 October 2021. Retrieved 7 October 2021.
  21. 1 2 Paras, Nick A.; MacMillan, David W. C. (12 June 2002). "The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes". Journal of the American Chemical Society. 124 (27). American Chemical Society (ACS): 7894–7895. doi:10.1021/ja025981p. ISSN   0002-7863. PMID   12095321.
  22. ↑ Jen, Wendy S.; Wiener, John J. M.; MacMillan, David W. C. (26 September 2000). "New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition". Journal of the American Chemical Society. 122 (40). American Chemical Society (ACS): 9874–9875. doi:10.1021/ja005517p. ISSN   0002-7863.
  23. ↑ Paras, Nick A.; MacMillan, David W. C. (13 April 2001). "New Strategies in Organic Catalysis: The First Enantioselective Organocatalytic Friedel−Crafts Alkylation". Journal of the American Chemical Society. 123 (18). American Chemical Society (ACS): 4370–4371. doi:10.1021/ja015717g. ISSN   0002-7863. PMID   11457218.
  24. ↑ Prier, Christopher K.; Rankic, Danica A.; MacMillan, David W. C. (19 March 2013). "Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis". Chemical Reviews. 113 (7): 5322–5363. doi:10.1021/cr300503r. ISSN   0009-2665. PMC   4028850 . PMID   23509883.
  25. ↑ Shaw, Megan H.; Twilton, Jack; MacMillan, David W. C. (19 August 2016). "Photoredox Catalysis in Organic Chemistry". The Journal of Organic Chemistry. 81 (16): 6898–6926. doi:10.1021/acs.joc.6b01449. ISSN   0022-3263. PMC   4994065 . PMID   27477076.
  26. ↑ Nicewicz, David A.; MacMillan, David W. C. (3 October 2008). "Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes". Science. 322 (5898): 77–80. Bibcode:2008Sci...322...77N. doi:10.1126/science.1161976. PMC   2723798 . PMID   18772399.
  27. ↑ David MacMillan publications indexed by Google Scholar OOjs UI icon edit-ltr-progressive.svg
  28. ↑ David MacMillan publications indexed by the Scopus bibliographic database. (subscription required)
  29. ↑ "Nobel Prize Dialogue – Criando nosso futuro junto com a ciência" (in Brazilian Portuguese). Retrieved 13 April 2024.
  30. ↑ Mesquita, Diego (13 April 2024). "Botafogo recebe vencedor do Prêmio Nobel de Química para visita à sede de General Severiano". Fogo na Rede (in Brazilian Portuguese). Retrieved 13 April 2024.
  31. ↑ "No. 63714". The London Gazette (Supplement). 1 June 2022. p. B2.
  32. ↑ Newsroom, The (8 June 2022). "Nobel prize winning chemist from Bellshill has now been knighted by the Queen". GlasgowWorld. Retrieved 9 June 2022.{{cite news}}: |last= has generic name (help)
  33. ↑ "MacMillan Awarded Sloan Research Fellowship". California Institute of Technology. August 2002. Retrieved 6 October 2021.
  34. ↑ "Caltech Faculty Awards and Honors 2004–2005" (PDF). California Institute of Technology. Archived from the original (PDF) on 11 August 2011. Retrieved 20 June 2012.
  35. ↑ "New Fellows 2012". Royal Society. Retrieved 20 June 2012.
  36. ↑ "Sir David MacMillan's Royal Society Fellowship Biography". The Royal Society. Retrieved 18 June 2022.
  37. ↑ "David W.C. MacMillan". American Academy of Arts & Sciences. Retrieved 15 June 2020.
  38. ↑ "Professor David William Cross MacMillan FRS, CorrFRSE – The Royal Society of Edinburgh". The Royal Society of Edinburgh. Retrieved 1 February 2018.
  39. ↑ "Past Recipients of the Harrison Howe Award" . Retrieved 7 October 2021.
  40. ↑ "The Society of SynthRyoji Noyori Prize Recipients". www.ssocj.jp (in Japanese). Society of Synthetic Organic Chemistry, Japan. Archived from the original on 22 October 2017. Retrieved 2 November 2017.
  41. ↑ "MacMillan To Laud Graduates' Resilience". NC State News. 1 May 2024. Retrieved 4 May 2024.
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