The Nobel Prize in Chemistry 2021 has been awarded jointly to
- Benjamin List, Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany, and
- David MacMillan, Princeton University, Princeton, NJ, USA
“for the development of asymmetric organocatalysis”.
Research
The type of catalysis developed independently by Benjamin List and David MacMillan, called organocatalysis, uses small organic molecules that are generally both environmentally friendly and inexpensive to produce. The use of organocatalysts has rapidly expanded since 2000. This is largely due to their ability to drive asymmetric synthesis. List and MacMillan have shown that organic catalysts can be used for a wide range of chemical reactions. Using this approach, researchers can construct anything from new drugs to molecules that can capture light in solar cells.
Benjamin List
Many enzymes catalyze chemical reactions without the help of metals. Instead, the reactions are mostly driven by a small number of amino acids in the enzyme. Benjamin List wondered whether amino acids have to be part of an enzyme to catalyze a chemical reaction. He tested whether proline could catalyze an intermolecular aldol reaction—which it did. List showed not only that proline is an efficient catalyst, but also that it can be used in asymmetric catalysis. Compared to metals and enzymes, proline is very simple, cheap, and environmentally friendly.
David MacMillan
David MacMillan had worked on improving asymmetric catalysis using metals. However, many metal-based catalysts are easily destroyed by moisture, which hinders their use in large-scale industrial manufacturing. MacMillan developed simple organic molecules that could temporarily provide or accommodate electrons—similar to metals. This was achieved by choosing compounds that can form an iminium ion. He found that a chiral imidazolidinone can catalyze a Diels-Alder reaction between α,β-unsaturated aldehydes and cyclopentadiene in this way. MacMillan coined the term organocatalysis to describe the general method.
Laureates
Benjamin List, born 1968 in Frankfurt am Main, Germany, studied chemistry at the Freie Universität Berlin, Germany, and was awarded his Ph.D. from the University of Frankfurt, Germany, in 1997 for work supervised by Johann Mulzer. From 1997 to 1998, he was a postdoctoral researcher with Richard Lerner and Carlos F. Barbas III at The Scripps Research Institute, La Jolla, CA, USA. In 1999, he was made Assistant Professor at the same institution. In 2003, he joined the Max Planck Institute for Coal Research, where he is currently Managing Director of the Institute and Director of the Department of Homogeneous Catalysis.
List was a visiting professor at Gakushuin University, Tokyo, Japan, in 2005, and at Sungkyunkwan University, South Korea, in 2008. Since 2004, he has been an Honorary Professor at the University of Cologne (Institute of Organic Chemistry), Germany.
Among many other awards, Benjamin List received the Carl Duisberg Memorial Prize of the German Chemical Society (GDCh) in 2003, the Otto Bayer Prize in 2012, and the Gottfried Wilhelm Leibniz Prize in 2016. In 2018, he was elected a Member of the German Academy of Sciences Leopoldina.
David W.C. MacMillan, born in 1968 in Bellshill, UK, studied chemistry at the University of Glasgow, UK. He received his Ph.D. in 1996 from the University of California, Irvine, USA, under the supervision of Larry Overman. From 1996 to 1998, he performed postdoctoral research with Professor Dave Evans at Harvard University, Cambridge, MA, USA. He then started his independent career at the University of California, Berkeley, USA. MacMillan joined the California Institute of Technology (Caltech), Pasadena, USA, in 2000, and was appointed Earle C. Anthony Chair of Organic Chemistry there in 2004. In 2006, he was appointed A. Barton Hepburn Professor of Chemistry and Director of the Merck Center for Catalysis at Princeton University, NJ, USA. In 2001, MacMillan became James S. McDonnell Distinguished University Professor of Chemistry at Princeton University.
Among other awards, David W.C. MacMillan received the Ryoji Noyori Prize in 2017, the Harrison Howe Award in 2015, and the Corday-Morgan Medal of Royal Institute of Chemistry in 2004. He is a Fellow of the Royal Society (FRS), a Member of the American Academy of Arts and Sciences and a Member of the National Academy of Sciences.
Award Ceremony
Traditionally, the award ceremonies take place in Stockholm, Sweden, on December 10—the anniversary of Alfred Nobel’s death. This year, the Laureates will receive their medals and diplomas in their home countries, and the traditional banquet will not take place due to the coronavirus pandemic. Last year was the first time since 1956 that the banquet was canceled, also because of the pandemic. In 1956, the banquet was suspended to avoid having to invite the Soviet ambassador after the USSR invaded Hungary.
Selected Publications by Benjamin List
- Catalytic Asymmetric Three-Component Synthesis of Homoallylic Amines,
S. Gandhi, B. List,
Angew. Chem. Int. Ed. 2013, 52, 2573–2576.
https://doi.org/10.1002/anie.201209776 - Organotextile Catalysis,
J.-W. Lee, T. Mayer-Gall, K. Opwis, C. E. Song, J. S. Gutmann, B. List,
Science 2013, 341, 1225–1229.
https://doi.org/10.1126/science.1242196 - Asymmetric Counteranion-Directed Catalysis: Concept, Definition, and Applications,
M. Mahlau, B. List,
Angew. Chem. Int. Ed. 2013, 52, 518–533.
https://doi.org/10.1002/anie.201205343 - Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals,
J.-W. Lee, B. List,
J. Am. Chem. Soc. 2012, 134, 18245–18248.
https://doi.org/10.1021/ja3096202 - Asymmetric spiroacetalization catalysed by confined Brønsted acids,
I. Čorić, B. List,
Nature 2012, 483, 315–319.
https://doi.org/10.1038/nature10932 - Direct Asymmetric α-Benzoyloxylation of Cyclic Ketones,
O. Lifchits, N. Demoulin, B. List,
Angew. Chem. Int. Ed. 2011, 50, 9680–9683.
DOI: 10.1002/anie.201104244 - A Highly Enantioselective Overman Rearrangement through Asymmetric Counteranion-Directed Palladium Catalysis,
G. Jiang, R. Halder, Y. Fang, B. List,
Angew. Chem. Int. Ed. 2011, 50, 9752–9755.
DOI: 10.1002/anie.201103843 - Proline-catalysed Mannich reactions of acetaldehyde,
J. W. Yang, C. Chandler, M. Stadler, D. Kampen, B. List,
Nature 2008, 452, 453–455.
https://doi.org/10.1038/nature06740 - Proline-Catalyzed Direct Asymmetric Aldol Reactions,
B. List, R. A. Lerner, C. F. Barbas,
J. Am. Chem. Soc. 2000, 122, 2395–2396.
https://doi.org/10.1021/ja994280y - Asymmetric enamine catalysis,
S. Mukherjee, J. W. Yang, S. Hoffmann, B. List,
Chem. Rev. 2007, 107, 12, 5471–5569.
https://doi.org/10.1021/cr0684016 - The Direct Catalytic Asymmetric Three-Component Mannich Reaction,
B. List,
J. Am. Chem. Soc. 2000, 122, 9336–9337.
https://doi.org/10.1021/ja001923x - Aldolase Antibodies of Remarkable Scope,
T. Hoffmann, G. Zhong, B. List, D. Shabat, J. Anderson, S. Gramatikova, R. A. Lerner, C. F. Barbas,
J. Am. Chem. Soc. 1998, 120, 2768–2779.
https://doi.org/10.1021/ja973676b - 3.0.CO;2-%23″ target=”_blank”>https://doi.org/10.1002/(SICI)1521-3765(19980515)4:5<881::AID-CHEM881>3.0.CO;2-%23
Selected Publications by David W. C. MacMillan
- Metallaphotoredox-Catalyzed Cross-Electrophile Csp3–Csp3 Coupling of Aliphatic Bromides,
Russell T. Smith, Xiaheng Zhang, Juan A. Rincón, Javier Agejas, Carlos Mateos, Mario Barberis, Susana García-Cerrada, Oscar de Frutos, David W. C. MacMillan,
J. Am. Chem. Soc. 2018, 140, 17433–17438.
https://doi.org/10.1021/jacs.8b12025 - Metallaphotoredox Difluoromethylation of Aryl Bromides,
Vlad Bacauanu, Sébastien Cardinal, Motoshi Yamauchi, Masaru Kondo, David F. Fernández, Richard Remy, David W. C. MacMillan,
Angew. Chem. Int. Ed. 2018, 57, 12543–12548.
https://doi.org/10.1002/anie.201807629 - Direct arylation of strong aliphatic C–H bonds,
Ian B. Perry, Thomas F. Brewer, Patrick J. Sarver, Danielle M. Schultz, Daniel A. DiRocco, David W. C. MacMillan,
Nature 2018, 560, 70–75.
https://doi.org/10.1038/s41586-018-0366-x - Visible Light Photoredox Catalysis with Transition Metal Complexes: Applications in Organic Synthesis,
Christopher K. Prier, Danica A. Rankic, David W. C. MacMillan,
Chem. Rev. 2013, 113, 5322–5363.
https://doi.org/10.1021/cr300503r - Enantioselective α-Arylation of Aldehydes via Organo-SOMO Catalysis. An Ortho-Selective Arylation Reaction Based on an Open-Shell Pathway,
J. C. Conrad, J. Kong, B. N. Laforteza, D. W. C. MacMillan,
J. Am. Chem. Soc. 2009, 131, 11640–11641.
https://doi.org/10.1021/ja9026902 - Merging Photoredox Catalysis with Organocatalysis: The Direct Asymmetric Alkylation of Aldehydes,
David A. Nicewicz, David W. C. MacMillan,
Science 2008, 322, 77–80.
https://doi.org/10.1126/science.1161976 - The advent and development of organocatalysis,
David W. C. MacMillan,
Nature 2008, 455, 304–308.
https://doi.org/10.1038/nature07367 - The First Enantioselective Organocatalytic Mukaiyama−Michael Reaction: A Direct Method for the Synthesis of Enantioenriched γ-Butenolide Architecture,
S. P. Brown, N. C. Goodwin, D. W. C. MacMillan,
J. Am. Chem. Soc. 2003, 125, 1192–1194.
https://doi.org/10.1021/ja029095q - The Enantioselective Organocatalytic 1,4-Addition of Electron-Rich Benzenes to α,β-Unsaturated Aldehydes,
N. A. Paras, D. W. C. MacMillan,
J. Am. Chem. Soc. 2002, 124, 7894–7895.
https://doi.org/10.1021/ja025981p
- New Strategies in Organic Catalysis: The First Enantioselective Organocatalytic Friedel−Crafts Alkylation,
N. A. Paras, D. W. C. MacMillan,
J. Am. Chem. Soc. 2001, 123, 4370–4371.
https://doi.org/10.1021/ja015717g
- New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder Reaction,
K. A. Ahrendt, C. J. Borths, D. W. C. MacMillan,
J. Am. Chem. Soc. 2000, 122, 4243–4244.
https://doi.org/10.1021/ja000092s
- New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar Cycloaddition,
W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan,
J. Am. Chem. Soc. 2000, 122, 9874–9875.
https://doi.org/10.1021/ja005517p
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ChemistryViews 2015.
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Angew. Chem. Int. Ed. 2017.
https://doi.org/10.1002/anie.201711047
