Department of Chemistry

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Kay M. Brummond

Professor

Contact

807 CHVRN
Chevron Science Center
219 Parkman Avenue

Pittsburgh, PA 15260
412-624-1955

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Research Overview

The Brummond research group focuses on several areas of organic chemistry, including total synthesis of natural products, transition-metal catalysis, cycloaddition reactions, and the design and synthesis of covalent modifiers. In total synthesis, they are applying the asymmetric Rh(I)-catalyzed allenic Pauson–Khand reaction (APKR) to prepare thapsigargin (Tg)–a natural product with sub-nanomolar activity against SERCA. Future directions involve designing and synthesizing Tg analogs guided by SAR data.  In transition metal catalysis, they are leveraging deep mechanistic insight gained through experiment and computation to design catalysts for increasing the scope of the asymmetric PKR of enynes. Future directions will incorporate modern statistical tools to facilitate rational catalyst design. In cycloaddition reactions, they are employing a multi-variate regression model for reactivity prediction of the dearomative dehydro-Diels–Alder reaction of heteroarenes. Future work will use these findings to synthesize new organic photovoltaics. In covalent modifiers, the group designs compounds inspired by natural products and uses the APKR to rapidly synthesize a 5,7,5-ring system with tunable thiol reactivity. Future directions will focus on identifying enzyme targets, including the SARS-CoV-2 main protease. 

 

The Brummond Lab is currently accepting new graduate students.

 

Complete Listing of Published Work in MyBibliography:

http://www.ncbi.nlm.nih.gov/myncbi/browse/collection/50348838/?sort=date...

Awards

  • 2022 Organic Syntheses, Board of Directors
  • 2021 American Association for the Advancement of Science (AAAS) Fellow
  • 2021 American Chemical Society Award for Encouraging Women into Careers in the Chemical Sciences sponsored by the Camille and Henry Dreyfus Foundation
  • 2020 Featured as Remarkable Woman in Organic Chemistry in ACS Symposium, see: https://www.organicdivision.org/blog/2020/04/29/virtual-symposium-april-29-2020/
  • 2019 Plenary Speaker at the National Organic Chemistry Symposium, see: https://www.organicdivision.org/nos-2019-lecture-videos/
  • 2018 Chancellor's Distinguished Public Service Award
  • 2018 Selected for Atlantic Coast Conference Academic Leaders Network Program
  • 2018 Provost's Spotlight on Women Leaders Series (https://www.youtube.com/watch?v=IUWCJeN3xwM&feature=youtu.be)
  • 2017 Executive Director of the 45th National Organic Symposium
  • 2016 Harold Kohn Endowed Alumni Lectureship awarded by Penn State University
  • 2016 Oxide Diversity Catalyst Lecture
  • 2015 ACS Pittsburgh Award
  • 2011 Visiting Fellow, University of New South Wales, Sydney, Australia
  • 2010 Visiting Professor, Université Pierre et Marie Curie-Paris 6, Paris, France
  • 2008 Visiting Professor, Department of Chemistry, MIT, Boston, MA
  • 2007 Carnegie Science Center Award-Emerging Female Scientist
  • 2007 American Chemical Society Akron Section Award
  • 2006–2008 Alternate Councilor, Division of Organic Chemistry-ACS, Elected
  • 2005–2009 NIH Synthetic and Biological Chemistry Study Section A, Permanent Member
  • 2006–2014 Board of Editors, Organic Syntheses
  • 2010 American Chemical Society Fellow
  • 2003 Chancellor’s Distinguished Research Award, Junior Scholar Awardee
  • 2002 Johnson & Johnson Focused Giving Award
  • 1999 Departmental Outstanding Faculty Award, Department of Chemistry, WVU
  • 1998 National Science Foundation-CAREER Award, (declined to accept NIH Award)

Publications

“A Celebration of the Publication of the 100th Volume of Organic Syntheses,” Margaret M. Faul* and Kay M. Brummond* J. Am. Chem. Soc. 2023, 145, 25509-25512
“Rhodium(I)-catalyzed Allenic Pauson–Khand Reaction,” Eric D. Deihl, Fatemeh Haghighi, Kay M. Brummond* Org. Synth. 2023, 100, 29
“Thiol Reactivity of N-Aryl α-Methylene-γ-Lactams: Influence of Guaianolide Structure,” Daniel P. Dempe, Chong-Lei Ji, Peng Liu,* and Kay M. Brummond* J. Org. Chem. 2022, 87, 11204–11217
“Rh(I)-Catalyzed Allenic Pauson–Khand Reaction to Access the Thapsigargin Core: Influence of Furan and Allenyl Chloroacetate Groups,” Eric D. Deihl, Luke T. Jesikowicz, Logan J. Newman, Peng Liu* and Kay M. Brummond* Organic Lett. 2022, 24 4, 959-999
“Origins of Enantioselectivity in the Rh(I)-catalyzed Pauson–Khand Reaction: Comparison of Bidentate and Monodentate Chiral Ligands,” Lauren C. Burrows, Luke T. Jesikowicz, Peng Liu* and Kay M. Brummond* ACS Catalysis 2021, 11, 323-336
“Synthesis of Guaianolide Analogues with a Tunable α-Methylene–γ-Lactam Electrophile and Correlating Bioactivity with Thiol Reactivity,” Paul A. Jackson, Henry A. M. Schares, Katherine F.M. Jones, John C. Widen, Daniel P. Dempe, Matthew E. Cuellar, Michael A. Walters, Daniel A. Harki* and Kay M. Brummond* J. Med. Chem 2020, 63, 14951-14978
“Metal Free C–C Coupling of Allenyl Sulfone with Picolyl Amides to Access Vinyl Sulfones via Pyridine-Initiated In Situ Generation of Sulfinate Anion,” Humair M. Omer, Peng Liu* and Kay M. Brummond* J. Org. Chem 2020, 85, 7959-7975
“Computationally Guided Catalyst Design in the Type I Dynamic Kinetic Asymmetric Pauson–Khand Reaction of Allenyl Acetates,” Lauren Parrette, Luke Jesikiewicz, Gang Lu, Steve Geib, Peng Liu,* Kay Brummond* J. Am. Chem. Soc. 2017, 139, 15022-15032.
“Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions,” Paul A. Jackson,† John C. Widen,‡ Daniel A. Harki,‡,*, and Kay M. Brummond,†* J. Med. Chem. 2017, 60, 839-885.
“Intramolecular Didehydro-Diels–Alder Reaction for the Synthesis of Benzo- and Dihydrobenzo-Fused Heterocycles,” Ashley Bober, Justin T. Proto, and Kay M. Brummond*. Org. Lett. 2017, 19, 1500-1503.
“Synthesis of Allenyl Mesylate by a Johnson-Claisen Rearrangement. Preparation of 3-(((Tert-butyldiphenylsilyl)oxy)methyl)penta-3,4-dien-1-yl Methanesulfonate,”  Joseph E. Burchick. Jr., Sarah M. Wells, and Kay M. Brummond,* Organic Syntheses. 2017, 94, 123.
“Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino and Carboxyl Groups via the Nicholas Reaction,” Sarah M. Wells,† John C. Widen,‡ Daniel A. Harki,‡* and Kay M. Brummond,†* Org. Lett. 2016, 18, 4566-4569.