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Keith Woerpel

Margaret & Herman Sokal Professor Of Medicinal Chemistry

    1991 …2020

    Research output per year

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    Research Output

    2020
    2019

    Cobalt-Catalyzed Intramolecular Silylperoxidation of Unsaturated Diisopropylsilyl Ethers

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

    Research output: Contribution to journalArticle

    Diastereoselective peroxidation of derivatives of Baylis–Hillman adducts

    Zuckerman, D. S. & Woerpel, K. A., Aug 2 2019, In : Tetrahedron. 75, 31, p. 4118-4129 12 p.

    Research output: Contribution to journalArticle

    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. A., Jan 1 2019, In : Synthesis (Germany). 51, 1, p. 296-302 7 p.

    Research output: Contribution to journalArticle

    2018

    Cobalt-Catalyzed Oxygenation/Dearomatization of Furans

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

    Research output: Contribution to journalArticle

    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. K., Woerpel, K. A. & Stockwell, B. R., May 1 2018, In : Nature Chemical Biology. 14, 5, p. 507-515 9 p.

    Research output: Contribution to journalArticle

    Mechanistic Insight into Additions of Allylic Grignard Reagents to Carbonyl Compounds

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

    Research output: Contribution to journalArticle

    2017

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

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

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

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

    Rotsides, C. Z. & Woerpel, K. A., Jan 1 2017, In : Dalton Transactions. 46, 27, p. 8763-8768 6 p.

    Research output: Contribution to journalArticle

    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. A. & Zhang, D. D., Oct 5 2017, In : Cell. 171, 2, p. 273-285 13 p.

    Research output: Contribution to journalReview article

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

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

    Research output: Contribution to journalReview article

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

    Sanzone, J. R. & Woerpel, K. A., Nov 13 2017, In : Synlett. 28, 18, p. 2478-2482 5 p.

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    2016

    [4+2] Cycloadditions of Seven-Membered-Ring trans-Alkenes: Decreasing Reactivity with Increasing Substitution of the Seven-Membered Ring

    Santucci, J., Sanzone, J. R. & Woerpel, K. A., Jan 1 2016, In : European Journal of Organic Chemistry. 2016, 17, p. 2933-2943 11 p.

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    Five-Membered Ring Peroxide Selectively Initiates Ferroptosis in Cancer Cells

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

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    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. A., Mar 2 2015, In : Angewandte Chemie - International Edition. 54, 10, p. 3061-3064 4 p.

    Research output: Contribution to journalArticle

    An SN1-type Reaction to Form the 1,2-Dioxepane Ring: Synthesis of 10,12-Peroxycalamenene

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

    Research output: Contribution to journalArticle

    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. A., Jun 5 2015, In : Organic Letters. 17, 11, p. 2704-2707 4 p.

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    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. A., Jan 1 2015, In : Journal of Organic Chemistry. 80, 1, p. 266-273 8 p.

    Research output: Contribution to journalArticle

    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

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

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

    Research output: Contribution to journalArticle

    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. A., Mar 21 2014, In : Organic Letters. 16, 6, p. 1566-1569 4 p.

    Research output: Contribution to journalArticle

    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. A., May 16 2014, In : Organic Letters. 16, 10, p. 2650-2653 4 p.

    Research output: Contribution to journalArticle

    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. A., Aug 15 2014, In : Organic Letters. 16, 16, p. 4280-4283 4 p.

    Research output: Contribution to journalArticle

    2013

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

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

    Research output: Contribution to journalArticle

    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. A., Aug 1 2012, In : Journal of the American Chemical Society. 134, 30, p. 12482-12484 3 p.

    Research output: Contribution to journalArticle

    2011
    2010

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

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

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    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. A., Aug 6 2010, In : Journal of Organic Chemistry. 75, 15, p. 5083-5091 9 p.

    Research output: Contribution to journalArticle

    Silylene transfer to allylic sulfides: Formation of substituted silacyclobutanes

    Ager, B. J., Bourque, L. E., Buchner, K. M. & Woerpel, K. A., Aug 20 2010, In : Journal of Organic Chemistry. 75, 16, p. 5729-5732 4 p.

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle

    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. A., May 21 2009, In : Organic Letters. 11, 10, p. 2173-2175 3 p.

    Research output: Contribution to journalArticle

    Correlations between nucleophilicities and selectivities in the substitutions of tetrahydropyran acetals

    Krumper, J. R., Salamant, W. A. & Woerpel, K. A., Nov 6 2009, In : Journal of Organic Chemistry. 74, 21, p. 8039-8050 12 p.

    Research output: Contribution to journalArticle

    Formation and utility of azasilacyclopentadienes derived from silacyclopropenes and nitriles

    Anderson, L. L. & Woerpel, K. A., Jan 15 2009, In : Organic Letters. 11, 2, p. 425-428 4 p.

    Research output: Contribution to journalArticle

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

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

    Research output: Contribution to journalArticle