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Synthesis

National Fresenius Award

by Melody M. Bomgardner
January 19, 2015 | APPEARED IN VOLUME 93, ISSUE 3

Doyle
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Credit: Denise Applewhite
09303-awards-doylecxd.jpg
Credit: Denise Applewhite

Sponsored by Phi Lambda Upsilon, the National Chemistry Honor Society

As a high school student, Abigail Doyle enjoyed all of her subjects—economics, literature, languages, and science. She was a serious musician and considered becoming a professional oboist. Luckily for chemistry, it was science that Doyle loved. Still, she can’t quite identify what inspired her to choose chemistry as her university major—before she even took her first college class.

Doyle, 34, entered Harvard University in 1998 and took organic chemistry in the spring. “Organic chemistry combines what I love about music and art and what I love about science, and it definitely resonated with me,” Doyle remembers. But it was getting into the lab that cemented a passion for chemical research. She interned at Bristol-Myers Squibb and pursued undergraduate research as a junior at Harvard.

The internship jump-started Doyle’s interest in medicinal and synthetic chemistry. Then, her undergraduate research drew her to transition-metal catalysis. Doyle graduated in 2002 with bachelor’s and master’s degrees in chemistry. She then went on to Stanford University to do a predoctoral fellowship in which she researched the hydration of unactivated alkenes catalyzed by gold complexes.

In 2003, Doyle returned to Harvard for Ph.D. work under adviser Eric N. Jacobsen. Her thesis focused on using alkyl halides and oxocarbenium ions in asymmetric catalysis. While at Harvard, she coauthored an article in Chemical Reviews on hydrogen-bond donor catalysis that has received more than 1,000 citations (2007, DOI: 10.1021/cr068373r).

From Harvard, Doyle was hired as an assistant professor of chemistry at Princeton University. In 2013, she became an associate professor and has continued her in-depth studies of transition-metal catalysis. One area of research that has been particularly fruitful has been fluorination chemistry. Doyle learned from friends in the pharmaceutical industry that introducing fluorine into molecules was very difficult but also very important. What they needed were mild and selective catalytic methods, they told her. Doyle and her research team set to work.

“It is remarkable to consider that only a few catalytic methods exist for the asymmetric installation of fluoride onto carbogenic frameworks,” says David W. C. MacMillan, a professor of chemistry at Princeton. “The work that is coming out of Abby’s lab is a direct solution to this problem.”

A second area of research at Doyle’s lab is the use of iminium and oxonium substrates in enantioselective coupling reactions. “Abby’s transformation is now being used extensively” by several pharmaceutical companies, MacMillan says, even as additional papers are in press from the group.

Doyle says the reason for her success is that she had several encouraging mentors early on, including M. Christina White, who was a postdoctoral researcher at Harvard and is now a professor of chemistry at the University of Illinois, Urbana-Champaign. “Every place I’ve been I’ve had a great group of people supporting me,” Doyle says.

Now she has turned her attention to mentoring chemists in her own lab. Her research group includes 13 graduate students and three postdoctoral fellows, as well as undergraduate researchers.

Doyle will present her award address before the Division of Organic Chemistry.

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