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Publications

2020

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

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Photochemical C–H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization

 

Mark W. Campbell, Mingbin Yuan, Viktor C. Polites, Osvaldo Gutierrez*, and Gary A. Molander*

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General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis

Top Most Read Articles in December 2020.

 

Lei Guo, Mingbin Yuan, Yanyan Zhang, Fang Wang, Shengqing Zhu, Osvaldo Gutierrez, and Lingling Chu

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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.

"Featured in Org. Chem. Highlights: Reactions of Alkenes"

https://www.organic-chemistry.org/Highlights/2021/24May.shtm 

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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.  

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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. 

 

  • Highlighted in Chemistry World: LINK

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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.

  • Highlighted in SYNFACTS: LINK

  • Back Inside Cover

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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.

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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.

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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

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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.

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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.

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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.

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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

  • Highlighted in SYNFACTS by Paul Knochel and Juri Skotnitzki! LINK   

  • Highlighted: Top 10% most downloaded paper in a year!

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Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment

 

Gutierrez, O.; Hendrick, C. E.; Kozlowski, M. C.

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Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

Phelan, J. P.; Lang, S. B.; Compton, J. S.; Kelly, C. B.; Dykstra, R.; Gutierrez, O.; Molander, G. A.

  • Highlights: Featured in the top 10 "Most Read Articles" in July 2018! 

  • Highlighted in SYNFACTS by Paul Knochel and Moritz Balkenhohl! LINK

  • Highlighted in Organic Chemistry Portal by Reto Muellerl! LINK   

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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

 

Kim, B.-S.; Gutierrez, O.; Kozlowski, M.; Walsh, P. J.

2017

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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

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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.

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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.

  • 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.

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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.

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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.

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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.

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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

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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.

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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.

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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

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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.

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Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones

Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J.

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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.

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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.

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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.

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Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes

 

Felix, R. J.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.

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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

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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.

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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.

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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.

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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.

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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.

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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

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Origin of Stereoselectivity in the Imidazolidinone-Catalyzed Reductions of Cyclic α,β-Unsaturated Ketones


Osvaldo Gutierrez, Robert G. Iafe, and K. N. Houk

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