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ACS Award For Creative Work In Synthetic Organic Chemistry

Recipients are honored for contributions of major significance to chemistry

by Carmen Drahl
January 26, 2009 | A version of this story appeared in Volume 87, Issue 4

Credit: Courtesy of Hisashi Yamamoto
Credit: Courtesy of Hisashi Yamamoto

Sponsored by Aldrich Chemical Co.

Hisashi Yamamoto, Arthur Holly Compton Distinguished Professor of Chemistry at the University of Chicago, is being recognized for the development of designer catalysts and reagents for organic synthesis.

Yamamoto has discovered myriad organic reactions and reagents by tailoring the effects of Lewis and Brønsted acid reagents with cleverly designed ligands. This "designer" approach is a central tenet of modern catalysis, says Philip E. Eaton, emeritus professor of chemistry at the University of Chicago.

Yamamoto's ligands—often based on tartaric acid, amino acids, 1,1′-bi-2-naphthol, or 8-hydroxyquinoline—help metals carry out diverse transformations, including Michael additions, aldol reactions, and pinacol couplings. Yamamoto also developed an allylic organobarium reagent that today bears his name. Furthermore, he demonstrated that homochiral protecting groups serve as a versatile technology in asymmetric synthesis, including asymmetric cyclopropanation reactions, Michael additions, and carbonyl alkylations. "His research has resulted in a host of applications in asymmetric synthesis that outperform all others," says E. Peter Kündig, a professor in the University of Geneva's department of organic chemistry. Yamamoto has put his methods' performance to the test in tackling tough synthetic targets, including platensimycin and the polyprenoids (–)-chromazonarol, (+)-8-epi-puupehedione and (–)-11′-deoxytaondiol methyl ether.

Sometimes, Yamamoto's reagents have succeeded in altering fundamental reactivity. For example, his bulky Lewis acid reagent aluminum tris(2,6-diphenylphenoxide) shields carbonyl carbons from attack by nucleophiles. This permits alternative reaction pathways that can result in the loss of aromaticity, a highly challenging transformation.

In an extension of the designer approach, through a combined Lewis acid and Brøonsted acid catalyst system, Yamamoto's team precisely controlled the stereochemical outcome of Diels-Alder reactions. This work is an early example of tandem catalysis, in which two different functions are combined in one catalyst to achieve novel chemistry, Eaton says.

Yamamoto, 65, studied chemistry with Hitosi Nozaki at Kyoto University, in Japan, where he received a B.S. in 1967. Under the guidance of E. J. Corey, he received a Ph.D. in chemistry from Harvard University in 1971. Afterward, Yamamoto became a researcher at Toray Industries under Jiro Tsuji. He returned to academia in 1972 and held positions at Kyoto University, the University of Hawaii, and Nagoya University, in Japan, before assuming his current post at the University of Chicago in 2002.

"Hisashi is internationally recognized as a truly creative and prolific researcher," says Koichiro Oshima, a professor of chemistry at Kyoto University who was Yamamoto's first student. Indeed, Yamamoto has published nearly 500 original papers, and 65 of those were published after his move to Chicago.

Many awards have celebrated Yamamoto's work. He won the Prelog Medal in 1993, the Chemical Society of Japan Award in 1995, the Toray Science & Technology Award in 1997, the Max Tishler Prize in 1998, Le Grand Prix de la Foundation Maison de la Chimie in 2002, the National Prize of the Purple Medal (Japan) in 2002, the Molecular Chirality Award in 2003, the Yamada Prize in 2004, the Tetrahedron Prize in 2006, the Japan Academy Prize in 2007, and the Humboldt Research Award in 2007.

Yamamoto will present the award address before the Division of Organic Chemistry.


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