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Synthesis

Arthur C. Cope Scholar Awards

by Pat Short
February 25, 2008 | APPEARED IN VOLUME 86, ISSUE 8

Enders
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Credit: Courtesy of Dieter Enders
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Credit: Courtesy of Dieter Enders

This award is only the latest of a clutch of awards Dieter Enders, 61, has received, including the Leibniz Prize, the highest German scientific award; the first Yamada Prize, awarded by the Japan Research Foundation for Optically Active Compounds; the Max Planck Research Award of the Max Planck Society and the Alexander von Humboldt Foundation; and the Emil Fischer Medal of the German Chemical Society. He became an editor at the chemistry journal Synthesis in 1984 and was promoted to editor-in-chief in 1998.

Enders is full professor and director at the Institute for Organic Chemistry at Rhenish-Westphalian Technical University (RWTH) Aachen, in Germany. His work has led to more than 450 publications, 20 patents, and two books. All have built upon the expertise he has gained in synthesis, asymmetry, organometallics, bioactive compounds, and organocatalysis.

Enders received a Dipl.Chem. in 1972 and a Ph.D. in 1974 at Justus Liebig University, in Giessen, Germany, under the guidance of Dieter Seebach. In 1975, he was a postdoc at Harvard University, working with E. J. Corey. His career began while he was a student, as an instructor at Justus Liebig in 1971; in 1979, he became a lecturer there. From 1980 to 1985, he was a professor at the University of Bonn; and in 1985, he took up the professorship he currently holds at RWTH Aachen.

He chaired the Aachen section of the German Chemical Society in 1989-90. At RWTH Aachen he was speaker of chemistry in 1990-92 and senator in 1996-98.

According to one of his colleagues, Enders is one of the pioneers in asymmetric synthesis: "After his thesis on lithiated nitrosamines and postdoctoral work on dimethyl hydrazones, Enders started work with hydrazones prepared from proline using his SAMP/RAMP-methodology in parallel to the oxazoline method work of Albert I. Meyers in the U.S. and the t-leucine imine methods of Kenji Koga in Japan."

Enders' work indicated that C-C bond formations with high, enzymelike enantioselectivities, in a wide range of reactions, were possible. Enders and his coworkers made available for the first time numerous important classes of compounds of high diastereo- and enantiomeric purity, such as α-alkylated, thiolated, hydroxylated, aminated, iodinated, and silylated aldehydes and ketones, among others. This work featured the first enantioselective aldol and Mannich reactions. His hydrazone technology also enables a practical chromatographic resolution of aldehydes and ketones.

Besides this work, he and his colleagues also developed synthetic methods involving a wide variety of chirally modified lithiated compounds in a wide range of reactions.

Enders also developed enantioselective processes based on transition-metal chemistry. These include iron- and palladium-mediated reactions, zirconocene-imine complexes for electrophilic enolate chemistry, aldol additions involving titanium, epoxidations with zinc derivatives, and the first asymmetric catalyses with chiral carbene ligands on rhenium and ruthenium.

Enders "demonstrates the usefulness of his methods by applying them in the synthesis of numerous natural and physiologically active products," a colleague says. A notable case in point: His method has been used to synthesize a barkbeetle pheromone that is used in Germany and Switzerland for trapping these forest-destroying insects.

In recent years, Enders has moved into organocatalysis. In this field, he is pioneering the use of chiral N-heterocyclic carbenes as catalysts. Other highlights are asymmetric organocatalytic syntheses of carbohydrates, amino sugars, and phytosphingosines, employing the biomimetic C3 + Cn concept. A notable breakthrough, the colleague adds, came when his group described an enantioselective, organocatalytic, multicomponent domino reaction, in the course of which four stereocenters are created with excellent stereoselectivity.

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