No photo of Keith Woerpel

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

Filter
Article
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

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

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
2017

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

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

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
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

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
Acetals
Static Electricity
Electrostatics
Hydrolysis
Stabilization

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)

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

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
phosphine
Reducing Agents
Peroxides
Titanium
Hydrides
phosphine
Reducing Agents
Peroxides
Titanium
Hydrides
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

Strained organosilacyclic compounds: Synthesis of anti-Bredt olefins and trans-dioxasilacyclooctenes

Prévost, M., Ziller, J. W. & Woerpel, K., Oct 21 2010, In : Dalton Transactions. 39, 39, p. 9275-9281 7 p.

Research output: Contribution to journalArticle

Cycloparaffins
Epoxy Compounds
Alkenes
Aldehydes
Carbon
2009

Alkylidenesilacyclopropanes derived from allenes: Applications to the selective synthesis of triols and homoallylic alcohols

Buchner, K. M., Clark, T. B., Loy, J. M. N., Nguyen, T. X. & Woerpel, K., May 21 2009, In : Organic Letters. 11, 10, p. 2173-2175 3 p.

Research output: Contribution to journalArticle

triols
alcohols
Alcohols
flasks
synthesis

Formation of medium-sized nitrogen heterocycles from γ-silyloxy- γ-lactams

Leonard, N. M. & Woerpel, K., Sep 18 2009, In : Journal of Organic Chemistry. 74, 18, p. 6915-6923 9 p.

Research output: Contribution to journalArticle

Lactams
Nitrogen
Silanes
Alkaloids
Substitution reactions
Silanes
Chirality
Epoxy Compounds
Alkenes
Aldehydes
Silanes
Chirality
Epoxy Compounds
Alkenes
Aldehydes
Silanes
Chirality
Epoxy Compounds
Alkenes
Aldehydes
Silanes
Chirality
Epoxy Compounds
Alkenes
Aldehydes

Preparation of bicyclic 1,2,4-trioxanes from γ,δ-unsaturated ketones

Ramirez, A. P., Thomas, A. M. & Woerpel, K., Feb 5 2009, In : Organic Letters. 11, 3, p. 507-510 4 p.

Research output: Contribution to journalArticle

Alkenes
Ketones
hydrogen peroxide
entry
ketones

Silylene oxonium ylides: di-tert-butylsilylene insertion into C-O bonds

Bourque, L. E., Haile, P. A., Loy, J. M. N. & Woerpel, K., Jul 11 2009, In : Tetrahedron. 65, 28, p. 5608-5613 6 p.

Research output: Contribution to journalArticle

Silanes
Acetals
Ethers
Ether
hydronium ion

Silylene transfer to α-keto esters and application to the synthesis of γ-lactones

Howard, B. E. & Woerpel, K., Aug 15 2009, In : Tetrahedron. 65, 33, p. 6447-6453 7 p.

Research output: Contribution to journalArticle

Hydroxy Acids
Lactones
Esters
Metals
Coulomb interactions
Static Electricity
Electrostatics
Ions
Rhamnose
2008

C-glycosylation reactions of sulfur-substituted glycosyl donors: Evidence against the role of neighboring-group participation

Beaver, M. G., Billings, S. B. & Woerpel, K., Feb 13 2008, In : Journal of the American Chemical Society. 130, 6, p. 2082-2086 5 p.

Research output: Contribution to journalArticle

Glycosylation
Sulfur
Substitution reactions
Ions
Lewis Acids

Continuum of mechanisms for nucleophilic substitutions of cyclic acetals

Krumper, J. R., Salamant, W. A. & Woerpel, K., 2008, In : Organic Letters. 10, 21, p. 4907-4910 4 p.

Research output: Contribution to journalArticle

Stereoselectivity
acetals
Lewis Acids
Acetals
Nucleophiles

Dearomatization reactions of aryl-substituted silaaziridines

Nevárez, Z. & Woerpel, K., Oct 17 2008, In : Journal of Organic Chemistry. 73, 20, p. 8113-8115 3 p.

Research output: Contribution to journalArticle

Nitrogen
Carbon
Atoms
benzaldehyde

Intermolecular silacarbonyl ylide cycloadditions: A direct pathway to oxasilacyclopentenes

Bourque, L. E. & Woerpel, K., 2008, In : Organic Letters. 10, 22, p. 5257-5260 4 p.

Research output: Contribution to journalArticle

acetals
Carbonyl compounds
Acetals
carbonyl compounds
Alkynes
acetals
Acetals
carbohydrates
Substitution reactions
Carbohydrates