Issue Date: March 17, 2014
Arthur C. Cope Scholar Award: Tomislav Rovis
Tomislav Rovis, 45, professor of chemistry at Colorado State University, Fort Collins, has wasted no time making his mark on organic synthesis.
After completing a postdoc with David A. Evans at Harvard University in 2000, he joined the faculty of Colorado State, an institution with a strong reputation in organic chemistry.
Before long, Rovis would prove to be an influential chemist in his own right, particularly in the use of nucleophilic carbenes as asymmetric catalysts. Rovis and collaborators published three papers in the Journal of the American Chemical Society in his second year at Colorado State. One of these papers, “A Highly Enantioselective Catalytic Intramolecular Stetter Reaction” (J. Am. Chem. Soc. 2002, DOI: 10.1021/ja027411v), has already been cited more than 250 times. “We felt we were getting things rolling,” he says. “It was a very exciting time to be in the group.”
Some of the best-known work from Rovis’s early days has to do with umpolung, a German term referring to the reversal of polarity of a functional group. Using nucleophilic carbene catalysts, Rovis’s group temporarily transformed the electrophilic carbon of an aldehyde into a nucleophile. “Making a molecule do something that it doesn’t want to do, that it is not built to do, is hard,” Rovis explains.
His most recent work has involved marrying the worlds of chemical and biochemical catalysis. In 2012, Rovis, working with Thomas R. Ward at the University of Basel, attached a rhodium cyclopentadienyl assembly to the protein streptavidin. The group used the resulting catalyst to react benzamide with alkene to make R enantiomers of dihydroisoquinolones. At around the same time, Baihua Ye and Nicolai Cramer at the Swiss Federal Institute of Technology, Lausanne, conducted the same reaction using a chiral rhodium catalyst.
“This is a seminal piece of science that is almost certain to inspire imitation,” said Justin Du Bois, an associate professor of chemistry at Stanford University and a specialist in synthesis, of Rovis’s work.
Rovis says the approach of artificially inserting catalytic metals into proteins could provide “a powerful tool for the future.” Enzymes, he points out, can only catalyze the reactions that they have evolved to catalyze. Metals, on the other hand, are immensely versatile. “That is why as synthetic chemists we have so much power,” he observes. “We can take advantage of the entire periodic table, not just carbon.” The technique can make metals even more powerful by opening up a whole new kind of ligand environment around them.
After discovering a fondness for chemistry in an organic chemistry class as a premed student at the University of Toronto, Rovis earned a B.S. in human biology in 1990. He earned a Ph.D. in organic chemistry under Mark Lautens, also at Toronto, in 1998.
Rovis believes organic synthesis will remain enchanting for future generations of scientists as well. “There is something special about creating a white powder and holding 10 g of it, in a flask or a vial, in your hand,” he observes. “People get the synthesis bug in that way, and that leads to interest in the field. This is still a very relevant area of science.”
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