Herbert C. Brown Award for Creative Work in Synthetic Methods

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.

Ronald Breslow Award for Achievement in Biomimetic Chemistry

Sponsored by the Ronald Breslow Endowment

Joanna Aizenberg marvels at the complex designs and structures of living things. She unlocks the secrets of how biological systems build with inorganic materials, then she works to reproduce these methods synthetically through chemical processes.

"Nature keeps surprising us," the Harvard University professor says of her quest for "biological approaches that endow a device or structure we can only dream of in a synthetic world."

Take the deep-sea sponge called Venus' flower basket. Aizenberg and colleagues at Lucent Technologies' Bell Labs found that this creature's skeleton, made up of glassy threads, is engineered for strength from the nanoscale to the macroscale level (C&EN, July 11, 2005, page 12).

Then there is the brittle star, a marine animal that's a cousin to starfish. Aizenberg discovered that the brittle star's skeleton, in addition to providing structural support for the creature, acts as a sophisticated lens that focuses light onto receptor cells in the animal's insides.

These, Aizenberg says, are examples of "biological solutions to complex problems in design of multifunctional materials."

Aizenberg's work could lead to design and development of biomimetic materials that could be used for safe and long-lasting repairs of teeth and bone, says Eleni Kousvelari, associate director for biotechnology and innovation at the National Institute of Dental & Craniofacial Research.

"To those who aim to design and develop bioinspired, nanostructured composite ceramic materials using principles from nature, her original studies on biomineralization are invaluable," Kousvelari says of Aizenberg's research.

George M. Whitesides, professor of chemistry and chemical biology at Harvard, calls Aizenberg "a star." He says of his former postgraduate researcher, "She is the world's leading and most innovative figure in biomineralization" and in understanding the calcium carbonate and silicate skeletons of simple organisms.

Whitesides says Aizenberg has created an "entirely new field by herself-understanding the multiple functions of the mineral skeletons of marine organisms."

Aizenberg, 48, spent nine years at Bell Labs, Murray Hill, N.J. Last year, she moved to Harvard, where she wears several hats. She is the Gordon McKay Professor of Materials Science and professor of chemistry and chemical biology. Plus, Aizenberg is the Susan S. & Kenneth L. Wallach Professor at the Radcliffe Institute for Advanced Study. Her research includes magnetic and optical properties of biological systems as well as nanoscale and subnanoscale designs.

Aizenberg says her interests in mathematics and physical sciences led to an undergraduate discipline that combines both-chemistry. She received a bachelor's in chemistry and a master's in physical chemistry from Moscow State University in what was then the Soviet Union. Aizenberg earned her doctorate at the Weizmann Institute of Science, in Rehovot, Israel, then worked two years as a postdoc at Harvard's department of chemistry and chemical biology under Whitesides.

In 1999, Aizenberg won the Arthur K. Doolittle Award given by the ACS Division of Polymeric Materials: Science & Engineering to authors of an outstanding paper presented before the division at each of the society's national meetings. She became a fellow of the American Association for the Advancement of Science in 2006.

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