Publications
2021
“Impact of Ligands and Metals on the Formation of Metallacyclic Intermediates and a Non-traditional Mechanism for Group VI Alkyne Metathesis Catalysts.”
Thompson, R. R.; Rotella, M. E.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O. Lee, S.
“Experimental and Computational Studies of the Mechanism of Iron-Catalysed C-H Activation/Functionalisation with Allyl Electrophiles.”
DeMuth, J. C.; Song, Z.; Carpenter, S. H.; Boddie, T. E.; Radovic, A.; Baker, T. M.; Gutierrez, O.; Neidig, M. L.
“Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor–Acceptor Complex Photoactivation.”
Lipp, A.; Badir, S.; Dykstra, R.; Gutierrez, O.; Molander, G. A.
Access to Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides
Toolika Agrawal, Robert T. Martin, Stephen Collins, Zachary Wilhelm, Mytia D. Edwards, Osvaldo Gutierrez*, and Joshua D. Sieber
Photochemical C–H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization
Mark W. Campbell, Mingbin Yuan, Viktor C. Polites, Osvaldo Gutierrez*, and Gary A. Molander*
2020
General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis
Lei Guo, Mingbin Yuan, Yanyan Zhang, Fang Wang, Shengqing Zhu, Osvaldo Gutierrez, and Lingling Chu
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Highlighted in SYNFACTS by Dirk Trauner amd Tongil Ko. PDF
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Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated Alkenes with Alkyl Halides and Grignard Reagents
Liu, L.; Lee, W.; Youshaw, C. R.; Yuan, M.; Geherty, M. B.; Zavalij, P. Y.; Gutierrez, O.
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Featured in Org. Chem. Highlights: Reactions of Alkenes" LINK
Oxidation of 8-Thioguanosine Gives Redox-Responsive Hydrogels and Reveals Intermediates in a Desulfurization Pathway
Xiao, S.; Lee, W.; Chen, F.; Zavalij, P. Y.; Gutierrez, O.; Davis, J.
Engaging a-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation.
Wang, H.; Liu, C.-F.; Song, Z.; Yuan, M.; Ho, Y. A.; Gutierrez, O.; Koh, M. J.
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Highlighted in Chemistry World: LINK
On the Nature of C(sp3)–C(sp2) Bond Formation in Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study of Ni/Photoredox Catalytic Cross-Coupling of Alkyl Radicals and Aryl Halides
Yuan, M.; Song, Z.; Badir, S. O.; Molander, G. A.; Gutierrez, O.
Photocatalyzed Diastereoselective Isomerization Of Cinnamyl Chlorides to Cyclopropanes
Xu, B.; Troian-Gautier, L.; Dykstra, R.; Martin, R.; Gutierrez, O.; Tambar, U. K.
Intra- and Intermolecular Fe-Catalyzed Dicarbofunctionalization of Vinyl Cyclopropanes
Liu, L.; Lee, W.; Yuan, M.; Acha, C.; Geherty, M. B.; Williams, B. Gutierrez, O.
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Highlighted in SYNFACTS by Paul Knochel and Simon Graßl : LINK
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Back Inside Cover
Mechanism of Iminium Salt-Catalyzed C(sp3)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction
Rotella, M. E.; Der, R.; Hilinski, M. K.; Gutierrez, O.
2019
Siloxide Podand Ligand as a Scaffold for Molybdenum Catalyzed Alkyne Metathesis and Isolation of a Dynamic Metallatetrahedrane Intermediate
Thompson, R. R.; Rotella, M. E.; Du, P.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O.; Lee, S.
Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis
Luo.; Gutierrez-Bonet, A.; Matsui, J. K.; Rotella, M. E.; Dykstra, R.; Gutierrez, O.; Molander, G. A.
The Role of Trichloroacetimidate To Enable Iridium-Catalyzed Regio- and Enantioselective Allylic Fluorination: A Combined Experimental and Computational Study
Sorlin, A. M.; Mixdorf, J. C.; Rotella, M.; Martin, R.; Gutierrez, O.; Nguyen, H. M.
The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry
Hyun, S.-M.; Yuan, M.; Maity, A.; Gutierrez, O.; Powers, D. C.
2018
Radical-clock α-halo-esters as mechanistic probes for bisphosphine iron-catalyzed cross-coupling reactions
Liu, L.; Lee, W.; Zhou, J.; Bandyopadhyay, S.; Gutierrez, O.
Mechanism of Nitrones and Allenoates Cascade Reactions for
the Synthesis of Dihydro[1,2-a]indoles
Lee, W.; Yuan, M.; Acha. C.; Onwu, A.; Gutierrez, O.
Templating and Catalyzing [2 + 2] Photocycloaddition in Solution Using a Dynamic G‐Quadruplex
Sutyak, K. B.; Lee, W.; Zavalij, P. V.; Gutierrez, O.; Davis, J. T.
Mechanisms of Bisphosphine Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions: Inner-Sphere or Outer-Sphere Arylation? (invited contribution)
Liu, L; Lee, W; Yuan, M.; Gutierrez, O.
Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insight
Matsui, J.; Gutierrez-Bonet, A.; Rotella, M.; Alam, R.; Gutierrez, O.; Molander, G. A
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Highlighted in SYNFACTS by Paul Knochel and Juri Skotnitzki! LINK
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Highlighted: Top 10% most downloaded paper in a year!
Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment
Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
Engaging Sulfinate Salts via Ni/Photoredox Dual Catalysis Enables Facile Csp2–SO2R Coupling
Cabrera-Afonso, M. J.; Lu,Z.-P.; Kelly, C. B.; Lang, S. B.; Dykstra, R.; Gutierrez, O.; Molander, G. A.
A Simple Procedure for the Synthesis of β -Hydroxyallenamides via Homoallenylation of Aldehydes
2017
Mechanism of Nakamura’s Bisphosphine Iron-Catalyzed Asymmetric C(sp2)-C(sp3) Cross-Coupling Reaction: The Role of Spin in Controlling Arylation Pathway
Lee, W.; Zhou, J.; Gutierrez, O.
Prior to the University of Maryland
A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl Compounds
Zhou, Y.; Gutierrez, O.; Sader, A. C.; Patel, N. D.; Fandrick, D. R.; Busacca, C. A.; Frandrick, K. R.; Kozlowski, M.; Senanayake, C. H. H.
Transition-metal-free chemo- and regioselective vinylation of azaallyls
Li, M.; Gutierrez, O.; Berritt, S.; Pascual-Escudero, A.; Yeşilçimen, A.; Yang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso,
E.; Kozlowski, M. C.; Walsh, P. J.
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Highlighted in Phys.Org
2016
Sequential C-H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor
Wei, X.;Qu, B.; Zeng, X.; Savoie, J.; Fandrick, K. R.; Desrosiers, J.-N.; Tcyrulnikov, S.; Marsini, M. A.; Buono, F. G.; Li, Z.; Yang, B.-S.
Nickel-Catalyzed C-3 Direct Arylation of Pyridinium Ions for the Synthesis of 1-Azafluorenes
Desrosiers, J. N.; Wei, X.; Gutierrez, O.; Savoie, J.; Qu, B.; Zeng, X.; Lee, H.; Grinberg, N.; Haddad, N.; Yee, N. K.; Roschangar, F.; Song, J. J.; Kozlowski, M. C.; Senanayake, C. H.
Application of a Computer-assisted Structure Elucidation Program for the Structural Determination of a New Terpenoid Aldehyde with an Unusual
Skeleton Li, X.-N.; Ridge, C. D.; Mazzola, E. P.; Sun, J.; Gutierrez, O.; Moser, A.; DiMartino, J. C.; MacDonald, S. A.; Chen, P.
Dynamically Complex [6+4] and [4+2] Cycloadditions in the Biosynthesis of Spinosyn A
Patel, A.; Chen, Z.; Yang, Z.; Gutierrez, O.; Liu, H.-v.; Houk, K. N.; Singleton, D. A.
Mechanism of Rh2(II)-Catalyzed Indole Formation—The Catalyst Does Not Control Product Selectivity
Harrison, G. J.; Gutierrez, O.; Jana, N.; Driver, T.; Tantillo, D. J.
2015
Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights
Wanner, B.; Kreituss, I.; Gutierrez, O.; Kozlowski, M. C.; Bode, J. W.
Nickel-Catalyzed Cross-Coupling of Photoredox Generated Radicals: Uncovering a General Manifold for Stereoconvergence in Nickel-Catalyzed Cross-Couplings
Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C.
Development and Origin of Diastereoselectivity of a Practical and Asymmetric Route to Sitagliptin and Derivatives
Gutierrez, O.; Dattatray, M.; Dwivedi, M.; Gudimalla, N.; Chandrashekar, E. R. R.; Vilas, D. H.; Bhattacharya, A.; Bandichhor, R.; Kozlowski, M. C.
Understanding Organometallic Reaction Mechanisms and Catalysis. Editor Valentin Ananikov. Wiley-VCH. Weinheim 2015.
Computational Studies on Sigmatropic Shifts via Alkene and Alkyne Activation by Palladium and Gold
Gutierrez, O.; Kozlowski, M. C.
2014
Concerted Amidation of Activated Esters: Reaction Path and Origins of Selectivity in the Kinetic Resolution of Cyclic Amines via NHC and Hydroxamic Acid Co-Catalyzed Acyl Transfer
Allen, S. E.; Hsieh, S.-Y.; Gutierrez, O.; Bode, J. W.; Kozlowksi, M. C.
Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J.
Stereocontrol in Asymmetric SE’ Reactions of γ-Substituted α,β-Unsaturated Aldehydes
Williams, D. R.; Atwater, B, A.; Ke, P.; Gutierrez, O.; Tantillo, D. J.
2013
Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins
Chen, M. Z.; Gutierrez, O.; Smith III, A. B.
Mechanism of Triflimide-Catalyzed [3,3]-Sigmatropic Rearrangements of
N-Allylhydrazones – Predictions and Experimental Validation
Gutierrez, O.; Strick, B, F.; Thomson, R. J.; Tantillo, D. J.
Carbonium vs. Carbenium Ion-like Transition State Geometries for Carbocation Cyclization – How Strain Associated with Bridging Affects 5-exo vs. 6-endo Selectivity
Gutierrez, O.; Harrison, J. G.; Felix, R. J.; Guzman, F. C.; Gagné, M. R.; Tantillo, D. J.
Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes
Felix, R. J.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the
Protodepalladation Steps
Dickstein, J. S.; Curto, J. M.; Gutierrez, O.; Mulrooney, C. A.; Kozlowski, M. C.
2012
A Au-Catalyzed Enantioselective Cope Rearrangement of Achiral 1,5- Dienes
Felix, R. J.; Weber, D.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
Analogies Between Synthetic and Biosynthetic Reactions in which [1,2]-Alkyl Shifts are Combined with Other Events-Dyotropic, Schmidt and Carbocation Rearrangements
Gutierrez, O.; Tantillo, D. J.
Reexamining the Mechanisms of Competing [3,3] and [3,5] Sigmatropic Shifts of 1,3,7 Octatriene
Gutierrez, O.; Harrison, J. G.; Pemberton, R. P.; Tantillo, D. J.
Stereocontrol in a Combined Allylic Azide Rearrangement and Intramolecular Schmidt Reaction: Application to Asymmetric Synthesis of Pinnaic Acid
Liu, R.; Gutierrez, O.; Tantillo, D. J.; Aubé, J.
Fragmentation of Oxime and Silyl-oxime Ether Odd-electron Positive Ions by the McLafferty Rearrangement: New Insights on Structural Factors that Promote α, β-Fragmentation
Laulhe, S.; Bogdanov, B.; Johannes, L. M.; Gutierrez, O.; Harrison, J. G.; Tantillo, D. J.; Zhang, X.; Nantz, M. H.
Mechanism of the Acid Promoted Intramolecular Schmidt Reaction. Theoretical Assessment of the Importance of Lone
Pair-Cation, Cation-pi and Steric Effects in Controlling Regioselectivity
Gutierrez, O.; Aubé, J.; Tantillo, D. J.
2010
Transition Metal Intervention for a Classic Reaction - Assessing the Feasibility of Ni(0)- promoted [1,3] Sigmatropic Shifts of Bicyclo[3.2.0]hept-2-enes
Gutierrez, O.; Tantillo, D. J.
Synthesis of a trans, syn, trans-Dodecahydrophenanthrene via a Bicyclic Transannular Diels-Alder Reaction: Intermediate for the Synthesis of Fusidic Acid
Jung, M E.; Zhang, T.-H.; Lui, R. M.; Gutierrez, O.; Houk, K. N.
Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes
Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan. D. W. C.
2009
Origin of Stereoselectivity in the Imidazolidinone-Catalyzed Reductions of Cyclic α,β-Unsaturated Ketones
Osvaldo Gutierrez, Robert G. Iafe, and K. N. Houk