Issue Date: March 17, 2014
Arthur C. Cope Mid Career Scholar Award: Benjamin List
Benjamin List, managing director of the Max Planck Institute for Coal Research in Mülheim, Germany, is a world leader in the field of organocatalysis. In particular, in 2000, he played the key part in establishing the role of proline—an amino acid—as a catalyst for intermolecular aldol reactions.
Throughout the 20th century, scientists published papers that mentioned examples of catalysis using small organic molecules, including amines. In particular, pharmaceutical industry groups led by Zoltan Hajos, who was then at Roche in Nutley, N.J., and Rudolf Wiechert of Schering AG in Berlin, described the use of proline for certain asymmetric intramolecular aldol reactions. But the reactions’ mechanics were ill defined, and they therefore had been widely viewed as exotic exceptions to the prevailing dogma that only enzymes and metal complexes can act as highly enantioselective, synthetically useful catalysts.
“List designed critical experiments that have eliminated some long-lasting confusions about the mechanisms of organocatalyzed reactions,” says Kendall N. Houk, chair of organic chemistry at the University of California, Los Angeles. He and List coedited a special issue of Accounts of Chemical Research on organocatalysis in 2004.
“In 2000, List published seminal publications on proline-catalyzed aldol and Mannich reactions that demonstrated that proline can be used in a general way as a catalyst for asymmetric synthesis,” says another academic from a prominent U.S. university who is familiar with List’s work. “Together with the independent work of other groups, this discovery set the foundation of modern organocatalysis.”
List’s discoveries have encouraged hundreds of researchers to join the field of organocatalysis, making it “a flourishing branch of chemistry producing thousands of publications annually,” the U.S. chemist adds. The combined work of the researchers, he notes, has resulted in industrial applications.
“Because of their rich chemistry as chiral catalysts, coupled with their stability, nontoxicity, greenness, and recyclability, chiral secondary amine catalysts are changing the way chiral molecules are made,” he further notes. “Major pharmaceutical, fragrance, and fine chemicals companies are all developing this technology.”
A native of Germany, List, 46, earned a Ph.D. from the University of Frankfurt in 1997. After a postdoc at Scripps Research Institute, La Jolla, Calif., he began his academic career there in 1999 as an assistant professor. He moved back to Germany in 2003 to take a position as an associate professor in the department of homogeneous catalysis at the Max Planck Institute for Coal Research. In 2005, he became a director there and in 2011 managing director of the institute.
An author of approximately 150 research papers that are cited on average more than 120 times each, List has won several awards for his pioneering contributions to organocatalysis, including the Mukaiyama Award in 2013, the Otto Bayer Award in 2012, and the AstraZeneca Research Award in Organic Chemistry in 2007. He is currently a regional editor at Synlett.
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