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Herbert C. Brown Award for Creative Work in Synthetic Methods

Recipients are honored for contributions of major significance to chemistry

by Amanda Yarnell
January 21, 2008 | A version of this story appeared in Volume 86, Issue 3

Credit: Harvard University
Credit: Harvard University

Sponsored by the Purdue Borane Research Fund and the Herbert C. Brown Award Endowment

"Eric N. Jacobsen is the preeminent developer of synthetic methods of his generation," says Stephen L. Buchwald of Massachusetts Institute of Technology.

At 47, Jacobsen, a professor of chemistry at Harvard University, "has discovered and used catalysts for effective and, in some cases, highly practical methods for enantioselective catalytic reactions such as epoxidations, hydrolysis, and carbon-carbon bond formation," adds K. C. Nicolaou of Scripps Research Institute. "Most significantly, Jacobsen's methods are applied by many, both in academia and industry, as the preferred processes to prepare enantiomerically pure or enriched materials."

Jacobsen's signature chiral metal salen catalysts are a case in point. Developed in the early 1990s, these inexpensive and easy-to-prepare catalysts now find widespread academic and industrial use for the enantioselective epoxidation of simple olefins. This asymmetric epoxidation reaction has been used on a multiton commercial scale for the preparation of a key intermediate in the synthesis of Crixivan, an HIV protease inhibitor drug.

His chiral metal salen catalysts for epoxide-ring opening have found widespread academic and commercial use for the kinetic resolution of terminal epoxides. These completely recyclable monomeric catalysts have been used to synthesize on the multiton scale several enantiomerically pure epoxides, including propylene oxide and epichlorohydrin. More recently, his lab has reported oligomeric versions of these catalysts with even better reactivity, substrate scope, and enantioselectivity.

In addition, the Jacobsen group has developed a number of chiral catalysts for highly enantioselective nucleophile-electrophile addition reactions. His class of chiral thiourea derivatives, which catalyze a range of asymmetric additions to amines, are widely used in total synthesis. And his chromium Schiff-base catalysts for the enantioselective cycloaddition of simple aldehydes and dienes or alkenes have found widespread use in natural product synthesis.

During his career, Jacobsen has also "defined several important principles for catalyst design that have had a strong influence on the field of organic chemistry," Buchwald notes.

For example, with his epoxidation catalysts, Jacobsen provided the first direct correlation between the electronic properties of a catalyst and its enantioselectivity. The idea that asymmetric catalysts' activity can be tuned via electronics "has since become a standard concept in the field," Buchwald says.

From mechanistic work with his oligomeric epoxide-ring-opening catalysts, Jacobsen and others helped define a bimetallic catalyst design strategy for asymmetric nucleophile-electrophile reactions. He has since shown that two different chiral metal complexes can cooperatively activate reactants in synthetically valuable catalytic transformations.

Jacobsen received a B.S. degree from New York University in 1982 and a Ph.D. from the University of California, Berkeley, in 1986. After a two-year postdoctoral stint at MIT, Jacobsen took a faculty position at the University of Illinois, Urbana-Champaign, in 1988. He joined Harvard as a full professor in 1993.

Among numerous other awards and honors, Jacobsen received an Arthur C. Cope Scholar Award in 1994 and the ACS Award for Creative Work in Organic Synthesis in 2001. He was elected a fellow of the American Association for the Advancement of Science in 2004.

The award address will be presented before the Division of Organic Chemistry.


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