David MacMillan

Last updated

David MacMillan

Born
David William Cross MacMillan

(1968-03-16) 16 March 1968 (age 53)
CitizenshipU.K., U.S. [1]
Education 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, Tristan Lambert
Website Official website

David William Cross MacMillan FRS FRSE (born 16 March 1968) [2] is a Scottish [3] [4] [5] [6] [7] [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]

Contents

Education and early life

MacMillan was born in Bellshill, Scotland in 1968 and grew in nearby New Stevenston. [12] He received his undergraduate degree in chemistry at the University of Glasgow, where he worked with Ernie Colvin. [13] [14]

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. [15] He earned his Ph.D. in 1996. [14]

He hailed his Scottish upbringing as a reason for him winning the Nobel. [12]

Career and research

Upon receiving his Ph.D., MacMillan accepted a 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). [14]

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. [14]

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

He is considered to be one of the founders of organocatalysis. [16] In 2000, MacMillan designed small organic molecules that can provide or accept electrons and therefore efficiently catalyse reactions. [16] [17] 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, or vice versa. [16] 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. [14] [16] He developed chiral imidazolidinone catalysts. [18] [17] [19] MacMillan catalysts  [ de ] are used in various asymmetric syntheses. Examples include Diels-Alder reactions, [17] 1,3-dipolar cycloadditions, [20] Friedel-Crafts alkylations [21] or Michael additions. [19]

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. [14]

Honours and awards

List

Related Research Articles

Enantioselective synthesis form of chemical synthesis

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.

Transfer hydrogenation is the addition of hydrogen (H2; dihydrogen in inorganic and organometallic chemistry) to a molecule from a source other than gaseous H2. It is applied in industry and in organic synthesis, in part because of the inconvenience and expense of using gaseous H2. One large scale application of transfer hydrogenation is coal liquefaction using "donor solvents" such as tetralin.

Organocatalysis 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 reaction in organic chemistry is a proline catalysed asymmetric aldol reaction. The reaction is named after its principal investigators, Zoltan Hajos others, from Hoffmann-La Roche and Schering AG. Discovered in the 1970s the original Hajos-Parrish catalytic procedure – shown in the reaction equation, leading to the optically active bicyclic ketol – paved the way of asymmetric organocatalysis. The Eder-Sauer-Wiechert modification lead directly to the optically active enedione, through the loss of water from the bicyclic ketol shown in figure.

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 applications.

Zoltan George Hajos is a Hungarian-born and trained American organic chemist. Originally an academic in his native Budapest, then an industrial chemist in the pharmaceutical industry, he is known for the Hajos–Parrish–Eder–Sauer–Wiechert reaction.

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.

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

Scott E. Denmark

Scott Eric Denmark is an American chemist who is the Reynold C. Fuson Professor of Chemistry at the University of Illinois at Urbana-Champaign (UIUC). Denmark received an S.B. degree from MIT in 1975 and the D.Sc.Tech. degree from ETH Zurich in 1980, under the supervision of Professor Albert Eschenmoser. He joined the faculty at UIUC the same year and became an associate professor in 1986, full professor in 1987, and was named the Fuson Professor of Chemistry in 1991. He served as the president and editor-in-chief of the Organic Reactions book series between 2008 and 2018. In 2017, Denmark was elected to the American Academy of Arts and Sciences. In 2018, he was elected to the National Academy of Sciences.

Ben Feringa Dutch Nobel laureate in chemistry

Bernard Lucas Feringa is a Dutch synthetic organic chemist, specializing in molecular nanotechnology and homogeneous catalysis. He is the Jacobus van 't Hoff Distinguished Professor of Molecular Sciences, at the Stratingh Institute for Chemistry, University of Groningen, Netherlands, and an Academy Professor of the Royal Netherlands Academy of Arts and Sciences. He was awarded the 2016 Nobel Prize in Chemistry, together with Sir J. Fraser Stoddart and Jean-Pierre Sauvage, "for the design and synthesis of molecular machines".

Abigail Gutmann Doyle is a Professor of Chemistry at the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. From 2017 to July 2021, she was the A. Barton Hepburn Professor of Chemistry at Princeton University, where she had served on the faculty since 2008. Her research focuses on the development of new chemical transformations in organic chemistry.

Clark Landis is an American chemist, whose research focuses on organic and inorganic chemistry. He is currently a Professor of Chemistry at the University of Wisconsin–Madison. He was awarded the ACS Award in Organometallic Chemistry in 2010, and is a fellow of the American Chemical Society and the American Association for the Advancement of Science.

Vy Maria Dong American chemist

Vy Maria Dong is a Vietnamese-American Professor of Chemistry at the University of California, Irvine (UCI). Dong works on enantioselective catalysis and natural product synthesis. She received the Royal Society of Chemistry's Merck, Sharp & Dohme Award in 2020, the American Chemical Society's Elias James Corey Award in 2019, and the UCI's Distinguished Alumni Award in 2018.

Sukbok Chang

Sukbok Chang is a South Korean organic chemist. He is a distinguished professor in the Department of Chemistry at Korea Advanced Institute of Science and Technology (KAIST). He is also the director of the Institute for Basic Science (IBS) Center for Catalytic Hydrocarbon Functionalizations (CCHF). He was an associate editor on ACS Catalysis and has served on the editorial advisory boards of The Journal of Organic Chemistry, Journal of the American Chemical Society, and Accounts of Chemical Research. His major research interest is transition metal catalyzed C-H bond functionalization for the carbon-carbon bond and carbon-heteroatom bond formation.

F. Dean Toste is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and Faculty Scientist at the Chemical Sciences Division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry and asymmetric ion-pairing catalysis. Toste was elected a member of the National Academy of Sciences in 2020, and a member of the American Academy of Arts and Sciences in 2018.

Dhevalapally B. Ramachary

Dhevalapally B. RamacharyFTAS, FRSC, FASc, FNASc, also known as D. B. Ramachary, is an Indian chemist and Professor at the School of Chemistry, University of Hyderabad. He has made numerous contributions in various fields of chemical science.

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.

Marisa C. Kozlowski is an American chemist who is Professor of Organic and Catalysis Chemistry at the University of Pennsylvania. Her research considers asymmetric synthesis and the development of cost effective catalysts. She was elected Fellow of the American Association for the Advancement of Science in 2012 and American Chemical Society in 2013.

Nitro-Mannich 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.

Benjamin List German chemist (born 1968)

Benjamin List is a German chemist who is one of the directors of the Max Planck Institute for Coal Research and professor of organic chemistry at the University of Cologne. He co-developed organocatalysis, a method of accelerating chemical reactions and making them more efficient. He shared the 2021 Nobel Prize in Chemistry with David MacMillan "for the development of asymmetric organocatalysis".

References

  1. "Princeton's David MacMillan receives Nobel Prize in chemistry". Princeton University. 6 October 2021. Retrieved 7 October 2021.
  2. Professor David MacMillan FRS
  3. https://www.bbc.co.uk/news/uk-scotland-58828279
  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. Retrieved 8 October 2021.
  8. "Princeton's David MacMillan receives Nobel Prize in chemistry". Princeton University. Retrieved 7 October 2021.
  9. "Home". Macmillan Group. Retrieved 15 June 2020.
  10. A short interview of Professor MacMillan is available on the Eminent Organic Chemists Page provided by the ACS Organic Division
  11. 1 2 "The Nobel Prize in Chemistry 2021". NobelPrize.org. Retrieved 6 October 2021.
  12. 1 2 "David MacMillan: 'Being Scottish helped me win Nobel Prize'". BBC News. 7 October 2021. Retrieved 7 October 2021.
  13. "Bellshill man and former Glasgow University student David WC MacMillan wins the Nobel prize for chemistry". Glasgow Times. Retrieved 7 October 2021.
  14. 1 2 3 4 5 6 7 "David MacMillan". National Academy of Sciences . Retrieved 7 October 2021.
  15. 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.
  16. 1 2 3 4 Castelvecchi, Davide; Stoye, Emma (6 October 2021). "'Elegant' catalysts that tell left from right scoop chemistry Nobel". Nature. Springer Science and Business Media LLC. doi:10.1038/d41586-021-02704-2. ISSN   0028-0836. PMID   34616090.
  17. 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. American Chemical Society (ACS). 122 (17): 4243–4244. doi:10.1021/ja000092s. ISSN   0002-7863.
  18. "David MacMillan". Princeton University Department of Chemistry. 21 July 2014. Retrieved 7 October 2021.
  19. 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. American Chemical Society (ACS). 124 (27): 7894–7895. doi:10.1021/ja025981p. ISSN   0002-7863. PMID   12095321.
  20. 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. American Chemical Society (ACS). 122 (40): 9874–9875. doi:10.1021/ja005517p. ISSN   0002-7863.
  21. 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. American Chemical Society (ACS). 123 (18): 4370–4371. doi:10.1021/ja015717g. ISSN   0002-7863. PMID   11457218.
  22. "MacMillan Awarded Sloan Research Fellowship". California Institute of Technology. August 2002. Retrieved 6 October 2021.
  23. "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.
  24. "New Fellows 2012". Royal Society. Retrieved 20 June 2012.
  25. "David W.C. MacMillan". American Academy of Arts & Sciences. Retrieved 15 June 2020.
  26. "Professor David William Cross MacMillan FRS, CorrFRSE – The Royal Society of Edinburgh". The Royal Society of Edinburgh. Retrieved 1 February 2018.
  27. "Past Recipients of the Harrison Howe Award" . Retrieved 7 October 2021.
  28. "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.