At the University of Maryland
Submitted
Published
21. Chem. Sci. 2020, ASAP. (First appeared inChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.12049377.v1).
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.
20. Chem. Commun. 2020, ACCEPTED.
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.
19. ACS Catal. 2020, 10, 4451-4459.
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
18. J. Am. Chem. Soc. 2020, 142, 7225-7234.
On The Nature of C(sp3)-C(sp2) Bond Formation In Nickel-Catalyzed Tertiary Radical Cross-Couplings: A Case Study Mechanistic
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.
-
Top-20 most read paper in April-May: LINK
17. J. Am. Chem. Soc. 2020, 142, 6206-6215.
Photocatalyzed Diastereoselective Isomerization Of Cinnamyl Chlorides to Cyclopropanes
Xu, B.; Troian-Gautier, L.; Dykstra, R.; Martin, R.; Gutierrez, O.; Tambar, U. K.
16. Chem. Sci. 2020, 11, 3146. (First appeared in ChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.9858500.v1).
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: LINK
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Back Inside Cover
15. ACS Catal. 2020, 10, 897-906.
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.
14. Organometallics 2019, 38, 4054-4059.
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.
13. ACS Catal. 2019, 9, 8835-8842.
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.
12. J. Am. Chem. Soc. 2019, 141, 14843-14852.
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.
10. Tetrahedron. 2018, 75, 129-136.
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.
09. Org. Biomol. Chem. 2018, 17, 1767-1772.
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.
08. Angew. Chem. Int. Ed. 2018, 57, 17146-17150.
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.
07. Comment. Inorg. Chem. 2018, 38, 210-237.
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.
06. Angew. Chem. Int. Ed. 2018, 57, 15847-15851.
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!
05. Org. Lett. 2018, 20 6539-6543.
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.
04. J. Am. Chem. Soc. 2018, 140, 8037-8047.
Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover
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
03. Chem. Sci. 2018, 9, 3186-3191.
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.
02. Adv. Synth. Catal. 2018, 360, 1426-1432.
A Simple Procedure for the Synthesis of β -Hydroxyallenamides via Homoallenylation of Aldehydes
Kim, B.-S.; Gutierrez, O.; Kozlowski, M.; Walsh, P. J.
2017
01. J. Am. Chem. Soc. 2017, 139, 16126-16133.
Lee, W.; Zhou, J.; Gutierrez, O.
PRE-University of Maryland
29. Org. Lett. 2017, 19, 5064-6067.
A Computational Investigation of the Ligand-Controlled Cu-Catalyzed Site-Selective Propargylation and Allenylation of Carbonyl
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.
28. Nature Chem. 2017, 9, 997-1004.
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 (link:
2016
27. J. Am. Chem. Soc. 2016, 138, 15473-15481.
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.; Tang, W.; Haddad, N.; Gutierrez, O.; Wang, J.; Lee, H.; Ma, S.; Campbell, S.; Lorenz, J. C.; Eckhardt, M.; Himmelsbach, F.;
Peters, S.; Patel, N. D.; Tan, Z.; Yee, N. K.; Song, J. J.; Roschangar, F.; Kozlowski, M. C.; Senanayake, C. H.
26. Chem. Sci, 2016, 7, 5581-5586.
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.
25. Magn. Reson. Chem. 2016, DOI: 10.1002/mrc.4466
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.
24. J. Am. Chem. Soc. 2016, 138, 3631-3634.
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.
23. J. Am. Chem. Soc. 2016, 138, 487-490.
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
22. J. Am. Chem. Soc. 2015, 137, 11491-11497.
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.
21. J. Am. Chem. Soc. 2015, 137, 4896-4899.
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.
20. Org. Lett. 2015, 17, 1742-1745.
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.
19. BOOK: 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
18. J. Am. Chem. Soc. 2014, 136, 11783-11791.
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.
17. Organometallics, 2014, 33, 5371-5377 .
Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones
Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J.
16. Org. Lett. 2014, 16, 468-471.
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
15. Angew. Chem. Int. Ed. 2013, 53, 1279-1282.
Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins
Chen, M. Z.; Gutierrez, O.; Smith III, A. B.
14. Chem. Sci. 2013, 4, 3997-4003.
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.
13. Chem. Sci. 2013, 4, 3894-3898.
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.
12. J. Org. Chem. 2013, 78, 5685-5690.
Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes
Felix, R. J.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
11. J. Org. Chem. 2013, 78, 4744-4761.
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
10. Nature Chem. 2012, 4, 405-409.
A Au-Catalyzed Enantioselective Cope Rearrangement of Achiral 1,5- Dienes
Felix, R. J.; Weber, D.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
09. J. Org. Chem. 2012, 77, 8845-8850.
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.
08. Chem. Eur. J. 2012, 18, 11029-11035.
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.
07. J. Am. Chem. Soc. 2012, 134, 6528-6531.
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.
06. J. Mass Spectrom. 2012, 47, 676-686.
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.
05. J. Org. Chem. 2012, 77, 640-647.
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
04. Organometallics 2010, 29, 3541-3545.
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.
03. J. Org. Chem. 2010, 75, 6933-6940.
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.
02. J. Am. Chem. Soc. 2010, 132, 6001-6005.
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
01.Org. Lett. 2009, 11, 4298-4301.
Origin of Stereoselectivity in the Imidazolidinone-Catalyzed Reductions of Cyclic α, β- Unsaturated Ketones
Gutierrez, O.; Iafe, R.; Houk, K. N.
