Abigail Doyle

Last updated
Abigail G. Doyle
Born (1980-04-30) April 30, 1980 (age 43)
Princeton, New Jersey, U.S.
CitizenshipAmerican
Alma mater Harvard University (BA, MA, PhD)
Parents
Awards Arthur C. Cope Scholar Award, Elias J. Corey Award
Scientific career
Fields Organic Chemistry, Organometallic chemistry, Catalysis
Institutions University of California, Los Angeles
Princeton University
Thesis Engaging alkyl halides and oxocarbenium ions in asymmetric catalysis  (2008)
Doctoral advisor Eric N. Jacobsen
Other academic advisors Justin DuBois
Notable students Julia Kalow
Website doyle.chem.ucla.edu

Abigail Gutmann Doyle is a professor of chemistry at the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. [1] Her research focuses on the development of new chemical transformations in organic chemistry.

Contents

Early life and education

Doyle was born in Princeton, NJ in 1980 to Michael W. Doyle and Amy Gutmann, the eighth president of the University of Pennsylvania and current United States Ambassador to Germany. Doyle studied chemistry as an undergraduate at Harvard University, graduating with A.B. and A.M. degrees summa cum laude in 2002.

After beginning graduate studies in the lab of Justin DuBois at Stanford University, Doyle completed her Ph.D. under Prof. Eric N. Jacobsen, where she developed enantioselective alkylations with tributyltin enolates catalyzed by a Cr(salen)Cl catalyst. [2] [3] She also worked on the development of an enantioselective addition of nucleophiles to oxocarbenium ions. [4]

Career

Independent career

In July 2008, Doyle was appointed as an assistant professor of chemistry at Princeton University. She was promoted to the rank of associate professor with tenure in 2013, and to full Professor with an endowed chair, the A. Barton Hepburn Professor of Chemistry, in 2017. [5] In 2021, she moved to the University of California, Los Angeles, where she holds the Saul Winstein Chair in Organic Chemistry. [1]

Research

A longstanding research interest of the Doyle group is the development of nickel-catalyzed C–C bond forming reactions that utilize unconventional cross-coupling electrophiles, such as epoxides, aziridines, imminium ions, and oxocarbenium ions. The group has developed and mechanistically interrogated new ligands and pre-catalysts for nickel, which have helped to enable these transformations. In collaboration with David MacMillan's group, the Doyle lab identified a new cross-coupling paradigm which allows the combination of photoredox and nickel catalysis. [6] The Doyle lab has subsequently applied Nickel/photoredox catalysis to methodologies involving both unconventional and traditional cross-coupling electrophiles.

The group has also been involved in the development of nucleophilic fluorination chemistry allowing the creation of pharmaceutically relevant molecules with sp3-C-F and sp2-C-F bonds. These methods have employed both transition metal and photoredox catalysis, and the group has developed new reagents for mild and selective deoxyfluorination reactions.

Recently, the Doyle group has worked in the area of data science-driven analysis of chemical reactions, including the implementation of machine learning algorithms to model and predict reaction outcome in organic chemistry. [7] [8] [9]

Awards and honors

Some key awards of Doyle's independent career include the Alfred P. Sloan Foundation Fellowship (Alfred P. Sloan Foundation, 2012), [10] Amgen Young Investigator Award (2012), Arthur C. Cope Scholar Award (American Chemical Society, 2014), [11] Bayer Early Excellence in Science Award (2013), Phi Lambda Upsilon National Fresenius Award (Phi Lamba Upsilon, 2014), Presidential Early Career Award for Scientists and Engineers (PECASE, 2014) BMS Unrestricted Grant in Synthetic Organic Chemistry (2016). [12]

She is currently Senior Editor, Accounts of Chemical Research . [13]

Related Research Articles

<span class="mw-page-title-main">Enamine</span> Class of chemical compounds

An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates.

In organic chemistry, a coupling reaction is a type of reaction in which two reactant molecules are bonded together. Such reactions often require the aid of a metal catalyst. In one important reaction type, a main group organometallic compound of the type R-M reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction.

<span class="mw-page-title-main">Biocatalysis</span> Use of natural catalysts to perform chemical transformations

Biocatalysis refers to the use of living (biological) systems or their parts to speed up (catalyze) chemical reactions. In biocatalytic processes, natural catalysts, such as enzymes, perform chemical transformations on organic compounds. Both enzymes that have been more or less isolated and enzymes still residing inside living cells are employed for this task. Modern biotechnology, specifically directed evolution, has made the production of modified or non-natural enzymes possible. This has enabled the development of enzymes that can catalyze novel small molecule transformations that may be difficult or impossible using classical synthetic organic chemistry. Utilizing natural or modified enzymes to perform organic synthesis is termed chemoenzymatic synthesis; the reactions performed by the enzyme are classified as chemoenzymatic reactions.

A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. The reaction is named after pinacol, which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859.

<span class="mw-page-title-main">Organocatalysis</span> Method in organic chemistry

In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds. Because of their similarity in composition and description, they are often mistaken as a misnomer for enzymes due to their comparable effects on reaction rates and forms of catalysis involved.

<span class="mw-page-title-main">David MacMillan</span> Scottish organic chemist

Sir David William Cross MacMillan is a Scottish chemist and the James S. McDonnell Distinguished University Professor of Chemistry at Princeton University, where he was also the chair of the Department of Chemistry from 2010 to 2015. He shared the 2021 Nobel Prize in Chemistry with Benjamin List "for the development of asymmetric organocatalysis". MacMillan used his share of the $1.14 million prize to establish the May and Billy MacMillan Foundation.

<span class="mw-page-title-main">Maurice Brookhart</span>

Maurice S. Brookhart is an American chemist, and professor of chemistry at the University of Houston since 2015.

Chiral Lewis acids (CLAs) are a type of Lewis acid catalyst. These acids affect the chirality of the substrate as they react with it. In such reactions, synthesis favors the formation of a specific enantiomer or diastereomer. The method is an enantioselective asymmetric synthesis reaction. Since they affect chirality, they produce optically active products from optically inactive or mixed starting materials. This type of preferential formation of one enantiomer or diastereomer over the other is formally known as asymmetric induction. In this kind of Lewis acid, the electron-accepting atom is typically a metal, such as indium, zinc, lithium, aluminium, titanium, or boron. The chiral-altering ligands employed for synthesizing these acids often have multiple Lewis basic sites that allow the formation of a ring structure involving the metal atom.

<span class="mw-page-title-main">Hydrogen auto-transfer</span>

Hydrogen auto-transfer, also known as borrowing hydrogen, is the activation of a chemical reaction by temporary transfer of two hydrogen atoms from the reactant to a catalyst and return of those hydrogen atoms back to a reaction intermediate to form the final product. Two major classes of borrowing hydrogen reactions exist: (a) those that result in hydroxyl substitution, and (b) those that result in carbonyl addition. In the former case, alcohol dehydrogenation generates a transient carbonyl compound that is subject to condensation followed by the return of hydrogen. In the latter case, alcohol dehydrogenation is followed by reductive generation of a nucleophile, which triggers carbonyl addition. As borrowing hydrogen processes avoid manipulations otherwise required for discrete alcohol oxidation and the use of stoichiometric organometallic reagents, they typically display high levels of atom-economy and, hence, are viewed as examples of Green chemistry.

Trifluoromethylation in organic chemistry describes any organic reaction that introduces a trifluoromethyl group in an organic compound. Trifluoromethylated compounds are of some importance in pharmaceutical industry and agrochemicals. Several notable pharmaceutical compounds have a trifluoromethyl group incorporated: fluoxetine, mefloquine, Leflunomide, nulitamide, dutasteride, bicalutamide, aprepitant, celecoxib, fipronil, fluazinam, penthiopyrad, picoxystrobin, fluridone, norflurazon, sorafenib and triflurazin. A relevant agrochemical is trifluralin. The development of synthetic methods for adding trifluoromethyl groups to chemical compounds is actively pursued in academic research.

In Lewis acid catalysis of organic reactions, a metal-based Lewis acid acts as an electron pair acceptor to increase the reactivity of a substrate. Common Lewis acid catalysts are based on main group metals such as aluminum, boron, silicon, and tin, as well as many early and late d-block metals. The metal atom forms an adduct with a lone-pair bearing electronegative atom in the substrate, such as oxygen, nitrogen, sulfur, and halogens. The complexation has partial charge-transfer character and makes the lone-pair donor effectively more electronegative, activating the substrate toward nucleophilic attack, heterolytic bond cleavage, or cycloaddition with 1,3-dienes and 1,3-dipoles.

<span class="mw-page-title-main">Hydrogen-bond catalysis</span>

Hydrogen-bond catalysis is a type of organocatalysis that relies on use of hydrogen bonding interactions to accelerate and control organic reactions. In biological systems, hydrogen bonding plays a key role in many enzymatic reactions, both in orienting the substrate molecules and lowering barriers to reaction. However, chemists have only recently attempted to harness the power of using hydrogen bonds to perform catalysis, and the field is relatively undeveloped compared to research in Lewis acid catalysis.

Asymmetric ion-pairing catalysis in chemistry is a type of asymmetric catalysis taking place specifically with charged intermediates or charged reagents. In one type of catalysis ion-pairing exists with a charged and chiral catalyst. The charged catalyst can be cationic or anionic. Catalysis by anionic catalysts is also called asymmetric counteranion-directed catalysis. In the other variation of asymmetric ion-pairing catalysis called anion or cation binding, the chiral catalyst is neutral but binds in a noncovalent way to an intermediate ion pair. Asymmetric ion-pairing catalysis is distinct from other covalent types of catalysis such as Lewis acid catalysis and Bronsted acid catalysis. It is one of several strategies in enantioselective synthesis and of some relevance to academic research.

<span class="mw-page-title-main">Synergistic catalysis</span>

Synergistic catalysis is a specialized approach to catalysis whereby at least two different catalysts act on two different substrates simultaneously to allow reaction between the two activated materials. While a catalyst works to lower the energy of reaction overall, a reaction using synergistic catalysts work together to increase the energy level of HOMO of one of the molecules and lower the LUMO of another. While this concept has come to be important in developing synthetic pathways, this strategy is commonly found in biological systems as well.

<span class="mw-page-title-main">Photoredox catalysis</span>

Photoredox catalysis is a branch of photochemistry that uses single-electron transfer. Photoredox catalysts are generally drawn from three classes of materials: transition-metal complexes, organic dyes, and semiconductors. While organic photoredox catalysts were dominant throughout the 1990s and early 2000s, soluble transition-metal complexes are more commonly used today.

Sarah Elizabeth Reisman is a Chemistry Professor at the California Institute of Technology. She received the (2013) Arthur C. Cope Scholar Award and the (2014) Tetrahedron Young Investigator Award for Organic Synthesis. Her research focuses on the total synthesis of complex natural products.

Heterobimetallic catalysis is an approach to catalysis that employs two different metals to promote a chemical reaction. Included in this definition are cases where: 1) each metal activates a different substrate, 2) both metals interact with the same substrate, and 3) only one metal directly interacts with the substrate(s), while the second metal interacts with the first.

F. Dean Toste is the Gerald E. K. Branch Distinguished Professor of Chemistry at the University of California, Berkeley and faculty scientist at the chemical sciences division of Lawrence Berkeley National Lab. He is a prominent figure in the field of organic chemistry and is best known for his contributions to gold chemistry and asymmetric ion-pairing catalysis. Toste was elected a member of the National Academy of Sciences in 2020, and a member of the American Academy of Arts and Sciences in 2018.

Thomas Lectka is an American organic chemist, academic and researcher. He is Jean and Norman Scowe Professor of Chemistry and leads the Lectka Group at Johns Hopkins University.

Louis Fensterbank is a French scientist specialized in molecular chemistry. Professor at Sorbonne University and Senior Member of Institut Universitaire de France, he has been the director of the Institut Parisien de Chimie Moléculaire since 2017.

References

  1. 1 2 Jennings, Penny (Jun 30, 2021). "Welcome Professor Abigail Doyle | UCLA Chemistry and Biochemistry". www.chemistry.ucla.edu. Retrieved 2021-07-01.
  2. ↑ Doyle, Abigail G.; Jacobsen, Eric N. (2005-01-01). "Enantioselective Alkylations of Tributyltin Enolates Catalyzed by Cr(salen)Cl: Access to Enantiomerically Enriched All-Carbon Quaternary Centers". Journal of the American Chemical Society. 127 (1): 62–63. doi:10.1021/ja043601p. ISSN   0002-7863. PMID   15631449.
  3. ↑ Doyle, Abigail G.; Jacobsen, Eric N. (2007). "Enantioselective Alkylation of Acyclic α,α-Disubstituted Tributyltin Enolates Catalyzed by a Cr(salen) Complex". Angewandte Chemie International Edition. 46 (20): 3701–3705. doi:10.1002/anie.200604901. ISSN   1521-3773. PMID   17407117.
  4. ↑ Reisman, Sarah E.; Doyle, Abigail G.; Jacobsen, Eric N. (2008-06-01). "Enantioselective Thiourea-Catalyzed Additions to Oxocarbenium Ions". Journal of the American Chemical Society. 130 (23): 7198–7199. doi:10.1021/ja801514m. ISSN   0002-7863. PMC   2574628 . PMID   18479086.
  5. ↑ The Doyle Group Archived 2017-11-14 at the Wayback Machine , Princeton University
  6. ↑ Zuo, Zhiwei; Ahneman, Derek T.; Chu, Lingling; Terrett, Jack A.; Doyle, Abigail G.; MacMillan, David W. C. (2014-07-25). "Merging photoredox with nickel catalysis: Coupling of α-carboxyl sp3-carbons with aryl halides". Science. 345 (6195): 437–440. Bibcode:2014Sci...345..437Z. doi:10.1126/science.1255525. ISSN   0036-8075. PMC   4296524 . PMID   24903563.
  7. ↑ Ahneman, Derek T.; Estrada, Jesus G. J.; Lin, Shishi; Dreher, Spencer D.; Doyle, Abigail G. (2018-02-15). "Predicting reaction performance in C–N cross-coupling using machine learning". Science. 360 (6385): 186–190. Bibcode:2018Sci...360..186A. doi: 10.1126/science.aar5169 . PMID   29449509. S2CID   206666015.
  8. ↑ Shields, Benjamin J.; Stevens, Jason; Li, Jun; Parasram, Marvin; Damani, Farhan; Martinez Alvarado, Jesus I.; Janey, Jacob M.; Adams, Ryan P.; Doyle, Abigail G. (2021-02-03). "Bayyesian reaction optimization as a tool for chemical synthesis". Nature. 590 (7844): 89–96. Bibcode:2021Natur.590...89S. doi:10.1038/s41586-021-03213-y. PMID   33536653. S2CID   231804657.
  9. ↑ Żurański, Andrzej M.; Martinez Alvarado, Jesus I.; Shields, Benjamin J.; Doyle, Abigail G. (2021-03-31). "Predicting Reaction Yields via Supervised Learning". Accounts of Chemical Research. 54 (8): 1856–1865. doi:10.1021/acs.accounts.0c00770. PMID   33788552. S2CID   232483029.
  10. ↑ "Past Fellows". sloan.org. Archived from the original on 2018-03-14. Retrieved 2018-09-02.
  11. ↑ Ritter, Stephen K. "2014 Arthur C. Cope Scholar Awards: Abigail G. Doyle | Chemical & Engineering News". cen.acs.org. Retrieved 2018-09-02.
  12. ↑ "Abigail Doyle | Princeton University Department of Chemistry". chemistry.princeton.edu. Retrieved 2020-10-27.
  13. ↑ "Editors". pubs.acs.org. Retrieved 2018-09-02.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.