Keith Woerpel

Margaret & Herman Sokal Professor Of Medicinal Chemistry

1991 …2019
If you made any changes in Pure, your changes will be visible here soon.

Research Output 1991 2019

2019

Cobalt-Catalyzed Intramolecular Silylperoxidation of Unsaturated Diisopropylsilyl Ethers

Oswald, J. P. & Woerpel, K., Jun 21 2019, In : Journal of Organic Chemistry. 84, 12, p. 7564-7574 11 p.

Research output: Contribution to journalArticle

Acetals
Ethers
Peroxides
Cobalt

Diastereoselective peroxidation of derivatives of Baylis–Hillman adducts

Zuckerman, D. S. & Woerpel, K., Jan 1 2019, In : Tetrahedron.

Research output: Contribution to journalArticle

Peroxides
Lactones
Cobalt
Derivatives

Diastereoselectivities in Reductions of α-Alkoxy Ketones Are Not Always Correlated to Chelation-Induced Rate Acceleration

Bartolo, N. D., Hornstein, A. L., Zhao, A. Y. & Woerpel, K., Jan 1 2019, In : Synthesis (Germany). 51, 1, p. 296-302 7 p.

Research output: Contribution to journalArticle

Chelation
Ketones
Reducing Agents
Reducing agents
Organometallics
2018

Cobalt-Catalyzed Oxygenation/Dearomatization of Furans

Oswald, J. P. & Woerpel, K., Aug 17 2018, In : Journal of Organic Chemistry. 83, 16, p. 9067-9075 9 p.

Research output: Contribution to journalArticle

Benzofurans
Furans
Thiophenes
Pyrroles
Oxygenation

FINO2 initiates ferroptosis through GPX4 inactivation and iron oxidation

Gaschler, M. M., Andia, A. A., Liu, H., Csuka, J. M., Hurlocker, B., Vaiana, C. A., Heindel, D. W., Zuckerman, D. S., Bos, P. H., Reznik, E., Ye, L. F., Tyurina, Y. Y., Lin, A. J., Shchepinov, M. S., Chan, A. Y., Peguero-Pereira, E., Fomich, M. A., Daniels, J. D., Bekish, A. V., Shmanai, V. V. & 4 others, Kagan, V. E., Mahal, L., Woerpel, K. & Stockwell, B. R., May 1 2018, In : Nature Chemical Biology. 14, 5, p. 507-515 9 p.

Research output: Contribution to journalArticle

Lipid Peroxides
Hydroxyl Radical
Lipid Peroxidation
Glutathione
Cell Death

Mechanistic Insight into Additions of Allylic Grignard Reagents to Carbonyl Compounds

Bartolo, N. D. & Woerpel, K., Sep 7 2018, In : Journal of Organic Chemistry. 83, 17, p. 10197-10206 10 p.

Research output: Contribution to journalArticle

Carbonyl compounds
Ketones
Reaction rates
Chlorides
2017

Additions of Organomagnesium Halides to α-Alkoxy Ketones: Revision of the Chelation-Control Model

Read, J. A., Yang, Y. & Woerpel, K., Jul 7 2017, In : Organic Letters. 19, 13, p. 3346-3349 4 p.

Research output: Contribution to journalArticle

chelation
Chelation
Ketones
ketones
halides

Allylmagnesium Halides Do Not React Chemoselectively because Reaction Rates Approach the Diffusion Limit

Read, J. A. & Woerpel, K., Feb 17 2017, In : Journal of Organic Chemistry. 82, 4, p. 2300-2305 6 p.

Research output: Contribution to journalArticle

Carbonyl compounds
Reaction rates
Bearings (structural)
Aldehydes
Esters

Diastereoselective silylene transfer reactions to chiral enantiopure alkenes: Effects of ligand size and substrate bias

Rotsides, C. Z. & Woerpel, K., 2017, In : Dalton Transactions. 46, 27, p. 8763-8768 6 p.

Research output: Contribution to journalArticle

Alkenes
Stereoselectivity
Metals
Ligands
Substrates

Ferroptosis: A Regulated Cell Death Nexus Linking Metabolism, Redox Biology, and Disease

Stockwell, B. R., Friedmann Angeli, J. P., Bayir, H., Bush, A. I., Conrad, M., Dixon, S. J., Fulda, S., Gascón, S., Hatzios, S. K., Kagan, V. E., Noel, K., Jiang, X., Linkermann, A., Murphy, M. E., Overholtzer, M., Oyagi, A., Pagnussat, G. C., Park, J., Ran, Q., Rosenfeld, C. S. & 7 others, Salnikow, K., Tang, D., Torti, F. M., Torti, S. V., Toyokuni, S., Woerpel, K. & Zhang, D. D., Oct 5 2017, In : Cell. 171, 2, p. 273-285 13 p.

Research output: Contribution to journalReview article

Cell death
Metabolism
Oxidation-Reduction
coenzyme Q10
Cell Death

Reactions of Allylmagnesium Halides with Carbonyl Compounds: Reactivity, Structure, and Mechanism

Bartolo, N. D., Read, J. A., Valentín, E. M. & Woerpel, K., Aug 1 2017, In : Synthesis (Germany). 49, 15, p. 3237-3246 10 p.

Research output: Contribution to journalReview article

Carbonyl compounds
Aldehydes
Ketones
Agglomeration
X rays
Alkenes
Alkynes
Electrons
Gases
Oxygen

Reactivity of Seven-Membered-Ring trans -Alkenes with Electrophiles

Sanzone, J. R. & Woerpel, K., May 10 2017, (Accepted/In press) In : Synlett.

Research output: Contribution to journalArticle

Alkenes
Alkynes
Electrons
Gases
Oxygen

Uncatalyzed Carboboration of Seven-Membered-Ring trans-Alkenes: Formation of Air-Stable Trialkylboranes

Sanzone, J. R., Hu, C. T. & Woerpel, K., Jun 28 2017, In : Journal of the American Chemical Society. 139, 25, p. 8404-8407 4 p.

Research output: Contribution to journalArticle

Alkenes
Olefins
Air
Silanes
Boron
2016
Cycloaddition
cycloaddition
Alkenes
alkenes
Substitution reactions

CuI-Catalyzed Synthesis of Propargyl Hydroperoxides Using Molecular Oxygen and Hydroxylamines

Miner, M. R. & Woerpel, K., Apr 1 2016, In : European Journal of Organic Chemistry. 2016, 10, p. 1860-1866 7 p.

Research output: Contribution to journalArticle

Hydroxylamines
Molecular oxygen
Hydrogen Peroxide
hydrazine
hydrazines

Five-Membered Ring Peroxide Selectively Initiates Ferroptosis in Cancer Cells

Abrams, R. P., Carroll, W. L. & Woerpel, K., May 20 2016, In : ACS Chemical Biology. 11, 5, p. 1305-1312 8 p.

Research output: Contribution to journalArticle

Peroxides
Cells
Lead compounds
Enantiomers
Cell death

High Reactivity of Strained Seven-Membered-Ring trans-Alkenes

Sanzone, J. R. & Woerpel, K., Jan 11 2016, In : Angewandte Chemie - International Edition. 55, 2, p. 790-793 4 p.

Research output: Contribution to journalArticle

Alkenes
Olefins
Quinones
Cycloaddition
Kinetics

Insertion reactions of silacyclopropanes: Evidence for a radical-based mechanism

Rotsides, C. Z. & Woerpel, K., Sep 26 2016, In : Organometallics. 35, 18, p. 3132-3138 7 p.

Research output: Contribution to journalArticle

Benzoquinones
Aldehydes
insertion
Stereoselectivity
Electrons
Ions
Stereoselectivity
Conformations
Ions
Stereoselectivity
Conformations
Ions
Stereoselectivity
Conformations
Ions
Stereoselectivity
Conformations

Stereoelectronic Model to Explain Highly Stereoselective Reactions of Seven-Membered-Ring Oxocarbenium-Ion Intermediates

Beaver, M. G., Buscagan, T. M., Lavinda, O. & Woerpel, K., Jan 26 2016, In : Angewandte Chemie - International Edition. 55, 5, p. 1816-1819 4 p.

Research output: Contribution to journalArticle

Ions
Stereoselectivity
Conformations
2015

Acceleration of acetal hydrolysis by remote alkoxy groups: Evidence for electrostatic effects on the formation of oxocarbenium ions

Garcia, A., Otte, D. A. L., Salamant, W. A., Sanzone, J. R. & Woerpel, K., Mar 2 2015, In : Angewandte Chemie - International Edition. 54, 10, p. 3061-3064 4 p.

Research output: Contribution to journalArticle

Acetals
Carbohydrates
Ionization
Electrostatics
Hydrolysis

An S<inf>N</inf>1-type Reaction to Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

Hilf, J. A., Witthoft, L. W. & Woerpel, K., Aug 21 2015, In : Journal of Organic Chemistry. 80, 16, p. 8262-8267 6 p.

Research output: Contribution to journalArticle

Sesquiterpenes
Peroxides
Cobalt
Biological Products
Functional groups

Copper(I)-catalyzed oxidation of alkenes using molecular oxygen and hydroxylamines: Synthesis and reactivity of α-oxygenated ketones

Andia, A. A., Miner, M. R. & Woerpel, K., Jun 5 2015, In : Organic Letters. 17, 11, p. 2704-2707 4 p.

Research output: Contribution to journalArticle

Hydroxylamines
Nucleophiles
Molecular oxygen
Balloons
Alkenes

Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes

Otte, D. A. L. & Woerpel, K., Aug 7 2015, In : Organic Letters. 17, 15, p. 3906-3909 4 p.

Research output: Contribution to journalArticle

aldehydes
Aldehydes
reagents
electron transfer
Electrons

Formation of an endoperoxide upon chromium-catalyzed allylic oxidation of a triterpene by oxygen

Chung, A., Miner, M. R., Richert, K. J., Rieder, C. J. & Woerpel, K., 2015, In : Journal of Organic Chemistry. 80, 1, p. 266-273 8 p.

Research output: Contribution to journalArticle

Triterpenes
Chromium
Oxygen
Oxidation
Catalytic oxidation

Formation of an endoperoxide upon chromium-catalyzed allylic oxidation of triterpene by oxygen

Chung, A., Miner, M. R., Richert, K. J., Rieder, C. J. & Woerpel, K., 2015, In : Journal of Organic Chemistry. 80, p. 266-273

Research output: Contribution to journalArticle

Acetals
Static Electricity
Electrostatics
Hydrolysis
Stabilization
Acetals
Nucleophiles
Isomers
Substitution reactions
Carbon

Structure and reactivity of an isolable seven-membered-ring trans-alkene

Hurlocker, B., Hu, C. & Woerpel, K., Mar 27 2015, In : Angewandte Chemie - International Edition. 54, 14, p. 4295-4298 4 p.

Research output: Contribution to journalArticle

Alkenes
Olefins
Single crystals
X rays
Geometry
2014

13C NMR spectroscopy for the quantitative determination of compound ratios and polymer end groups

Otte, D. A. L., Borchmann, D. E., Lin, C., Weck, M. & Woerpel, K., Mar 21 2014, In : Organic Letters. 16, 6, p. 1566-1569 4 p.

Research output: Contribution to journalArticle

Nuclear magnetic resonance spectroscopy
Polymers
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
nuclear magnetic resonance
Stereoselectivity
rigidity
Rigidity
Substitution reactions
Bearings (structural)
trichloroethylene
Glycosylation
Trichloroethylene
acetals
Acetals

Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones

Kandur, W. V., Richert, K. J., Rieder, C. J., Thomas, A. M., Hu, C., Ziller, J. W. & Woerpel, K., May 16 2014, In : Organic Letters. 16, 10, p. 2650-2653 4 p.

Research output: Contribution to journalArticle

Dioxolanes
Peroxides
Biological Products
Ketones
ketones

Synthesis of silyl monoperoxyketals by regioselective cobalt-catalyzed peroxidation of silyl enol ethers: Application to the synthesis of 1,2-dioxolanes

Hurlocker, B., Miner, M. R. & Woerpel, K., Aug 15 2014, In : Organic Letters. 16, 16, p. 4280-4283 4 p.

Research output: Contribution to journalArticle

Dioxolanes
Ethers
Molecular oxygen
Cobalt
ethers
2013
Stereochemistry
Epoxy Compounds
Aldehydes
Silver
Carbon
Stereochemistry
Epoxy Compounds
Aldehydes
Silver
Carbon

Nucleophilic addition to silyl-protected five-membered ring oxocarbenium ions governed by stereoelectronic effects

Tran, V. T. & Woerpel, K., Jul 5 2013, In : Journal of Organic Chemistry. 78, 13, p. 6609-6621 13 p.

Research output: Contribution to journalArticle

Ions
Furans
Deoxyribose
Acetals
Cations
2012

Diastereoselective synthesis of seven-membered-ring trans-alkenes from dienes and aldehydes by silylene transfer

Greene, M. A., Prévost, M., Tolopilo, J. & Woerpel, K., Aug 1 2012, In : Journal of the American Chemical Society. 134, 30, p. 12482-12484 3 p.

Research output: Contribution to journalArticle

Alkenes
Aldehydes
Olefins
Carbon
Silanes
Cyclohexanes
Alkenes
Ketones
Cyclohexenes
Bearings (structural)
2011
Carbonyl compounds
Aldehydes
Cycloparaffins
Stereoisomerism
Hot Temperature
2010

Erosion of stereochemical control with increasing nucleophilicity: O-glycosylation at the diffusion limit

Beaver, M. G. & Woerpel, K., Feb 19 2010, In : Journal of Organic Chemistry. 75, 4, p. 1107-1118 12 p.

Research output: Contribution to journalArticle

Glycosylation
Nucleophiles
Erosion
Stereoselectivity
Substitution reactions

Palladium- and nickel-catalyzed carbon-carbon bond insertion reactions with alkylidenesilacyclopropanes

Buchner, K. M. & Woerpel, K., Apr 12 2010, In : Organometallics. 29, 7, p. 1661-1669 9 p.

Research output: Contribution to journalArticle

Palladium
Nickel
palladium
insertion
Carbon
phosphine
Reducing Agents
Peroxides
Titanium
Hydrides
phosphine
Reducing Agents
Peroxides
Titanium
Hydrides

Phosphine-catalyzed reductions of alkyl silyl peroxides by titanium hydride reducing agents: Development of the method and mechanistic investigations

Harris, J. R., Haynes, M. T., Thomas, A. M. & Woerpel, K., Aug 6 2010, In : Journal of Organic Chemistry. 75, 15, p. 5083-5091 9 p.

Research output: Contribution to journalArticle

phosphine
Reducing Agents
Peroxides
Titanium
Hydrides