Independent Research
30. Wang, H.; Liu, C.F.; Martin, R. T.; Gutierrez, O.; # Koh, M. J. #
Submitted
“Directing Group-Free Alkene Dicarbofunctionalization.”
29.Review. Yuan, M.; Gutierrez, O.#
WIREs Computational Molecular Science. 2021, ACCEPTED.
“Mechanisms, Challenges, and Opportunities of Dual Ni/Photoredox Catalyzed C(sp2)-C(sp3) Cross-Couplings. ” (Invited Article)
28. Liu, C.F.; Wang, H.; Martin, R. T.; Gutierrez, O.; # Koh, M. J. #
Nat. Catal. 2021, 4, 674-683.
“A General Olefin Functionalization/Isomerization Strategy for Stereoselective Alkene Synthesis.”
27. Thompson, R. R.; Rotella, M. E.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O.# Lee, S.#
J. Am. Chem. Soc. 2021, 143, 9026-9039.
“Impact of Ligands and Metals on the Formation of Metallacyclic Intermediates and a Non-traditional Mechanism for Group VI Alkyne Metathesis Catalysts.”
26. DeMuth, J. C.; Song, Z.; Carpenter, S. H.; Boddie, T. E.; Radovic, A.; Baker, T. M.; Gutierrez, O.;# Neidig, M. L.#
Chem. Sci. 2021, 12, 9398-9407.
“Experimental and Computational Studies of the Mechanism of Iron-Catalysed C-H Activation/Functionalisation with Allyl Electrophiles.”
25. Lipp, A.; Badir, S.; Dykstra, R.; Gutierrez, O.;# Molander, G. A.#
Adv. Synth. Catal. 2021, 363, 3507-3520.
“Catalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor–Acceptor Complex Photoactivation.”
•Highlighted with VIP (Very Important Publication) designation
24. Agrawal, T.; Martin, R.; Collins, S.; Wilhelm, Z.; Edwards, M. D.; Gutierrez, O.;# Sieber, J. D. #
J. Org. Chem. 2021, 86, 5026-5046.
“Access To Chiral Diamine Derivatives through Stereoselective Cu-Catalyzed Reductive Coupling of Imines and Allenamides.”
23. Campbell, M. W.; Yuan, M.; Polites, V. C.; Gutierrez, O.;# Molander, G. A. #
J. Am. Chem. Soc. 2021, 143, 3901-3910.
“Photochemical C–H Activation Enables Nickel-Catalyzed Olefin Dicarbofunctionalization.”
22. Guo, L.; Yuan, M.; Zhang, Y.; Wang, F.; Zhu, S.; Gutierrez, O.# Chu, L. #
J. Am. Chem. Soc. 2020, 142, 20390-20399.
“General Method for Enantioselective Three-Component Carboarylation of Alkenes Enabled by Visible-Light Dual Photoredox/Nickel Catalysis.”
21. Liu, L.; Lee, W.; Youshaw, C. R.; Yuan, M.; Geherty, M. B.; Zavalij, P. Y.; Gutierrez, O.#
Chem. Sci. 2020, 11, 8301-8305.
“Fe-Catalyzed Three-Component Dicarbofunctionalization of Unactivated Alkenes with Grignard Reagents.”
•Featured in Org. Chem by Douglass F. Taber under Highlights: Reactions of Alkenes LINK
•Highlighted in Organic Chemistry Portal by Reto Muellerl! LINK
•Highlighted in SYNFACTS by Mark Lautens: LINK
20. Yuan, M.; Song, Z.; Badir, S. O.; Molander, G. A.; # Gutierrez, O.#
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.”
19. Liu, L.; Lee, W.; Yuan, M.; Acha, C.; * Geherty, M. B.; * Williams, B. * Gutierrez, O.#
Chem. Sci. 2020, 11, 3146-3151.
“Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes.”
•Highlighted in SYNFACTS: LINK
18. Rotella, M. E.; Der, R.; Hilinski, M. K.#; Gutierrez, O.#
ACS. Catal. 2020, 10, 1, 897-906.
“Mechanism of Iminium Salt-Catalyzed C(sp3)-H Amination: Factors Controlling Hydride Transfer versus H-Atom Abstraction.”
17. Xiao, S.; Lee, W.; Chen, F.; Zavalij, P. Y.; Gutierrez, O.; # Davis, J. #
Chem. Commun. 2020, 56, 6981-6984.
“Oxidation of 8-Thioguanosine Gives Redox-Responsive Hydrogels and Reveals Intermediates in a Desulfurization Pathway.”
16. Wang, H.; Liu, C.-F.; Song, Z.; Yuan, M.; Ho, Y. A.; Gutierrez, O.; # Koh, M. J. #
ACS Catal. 2020, 10, 4451-4459.
“Engaging a-Fluorocarboxylic Acids Directly in Decarboxylative C-C Bond Formation.”
•Highlighted in Chemistry World:LINK
15. Xu, B.; Troian-Gautier, L.; # Dykstra, R.; Martin, R.; Gutierrez, O.# Tambar, U. K. #
J. Am. Chem. Soc. 2020, 142, 6206-6215.
“Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes”
14. Thompson, R. R.; Rotella, M. E.; Du, P.; Zhou, X.; Fronczek, F. R.; Kumar, R.; Gutierrez, O.# Lee, S.#
Organometallics 2019, 38, 4054-4059.
“Siloxide Podand Ligand as a Scaffold for Molybdenum Catalyzed Alkyne Metathesis and Isolation of a Dynamic Metallatetrahedrane Intermediate.”
13. Luo. Y.; Gutierrez-Bonet, A.; Matsui, J. K.; Rotella, M. E.; Dykstra, R.; Gutierrez, O.;# Molander, G. A. #
ACS Catal. 2019, 9, 8835-8842.
“Oxa- and Azabenzonorbornadienes as Electrophilic Partners under Photoredox/Nickel Dual Catalysis.”
12. Sorlin, A. M.; Mixdorf, J. C.; Rotella, M.; Martin, R.;* Gutierrez, O.;# Nguyen, H. M. #
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.”
11. Hyun, S.-M.; Yuan, M.; Maity, A.; Gutierrez, O.;# Powers, D. C. #
Chem 2019, 5, 2388-2404.
“The Role of Iodanyl Radicals as Critical Chain Carriers in Aerobic Hypervalent Iodine Chemistry.”
10. Liu, L.; Lee, W.; Zhou, J.; Bandyopadhyay, S.; * Gutierrez, O.#
Tetrahedron 2019, 75, 129-136.
“Radical-clock α-halo-esters as mechanistic probes for bisphosphine iron-catalyzed cross-coupling reactions.”
9. Lee, W.; Yuan, M.; Acha. C.; * Onwu, A.; * Gutierrez, O.#
Org. Biomol. Chem. 2018, 17, 1767-1772.
“Mechanism of Nitrones and Allenoates Cascade Reactions for the Synthesis of Dihydro[1,2-a]indoles.”
8. Sutyak, K. B.; Lee, W.; Zavalij, P. V.; Gutierrez, O.;# Davis, J. T. #
Angew. Chem. Int. Ed. 2018, 57, 17146-17150.
“Templating and Catalyzing [2 + 2] Photocycloaddition in Solution Using a Dynamic G‐Quadruplex.”
7. Review. Liu, L; Lee, W; Yuan, M.; Gutierrez, O.#
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?”
6. Matsui, J. K.; Gutierrez-Bonet, A.; Rotella, M.; Alam, R.; Gutierrez, O.;# Molander, G. A. #
Angew. Chem. Int. Ed. 2018, 57, 15847-15851.
“Photoredox/Nickel-Catalyzed Single-Electron Tsuji-Trost Reaction: Development and Mechanistic Insight.”
•Highlighted in SYNFACTS by Paul Knochel and Juri Skotnitzki! LINK
•Highlighted as Top 10% most downloaded paper in a year!
5. Phelan, J. P.; Lang, S. B.; Compton, J. S.; Kelly, C. B.; Dykstra, R.; Gutierrez, O.; # Molander, G. A. #
J. Am. Chem. Soc. 2018, 140, 8037-8047.
“Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover.”
•Highlighted as 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
4. Cabrera-Afonso, M. J.; Lu,Z.-P.; Kelly, C. B.; Lang, S. B.; Dykstra, R.; Gutierrez, O.; # Molander, G. A. #
Chem. Sci. 2018, 9, 3186-3191.
“Engaging Sulfinate Salts via Ni/Photoredox Dual Catalysis Enables Facile Csp2–SO2R Coupling.”
3. Lee, W.; Zhou, J.; Gutierrez, O.; #
J. Am. Chem. Soc. 2017, 139, 16126-16133.
“Mechanism of Nakamura’s Iron-Catalyzed Asymmetric Cross-coupling Reaction: The Role of Spin in Controlling Selectivity.”
2. Li, X.-N.; Ridge, C. D.; # Mazzola, E. P.; Sun, J.; Gutierrez, O.; Moser, A.; DiMartino, J. C.; MacDonald, S. A.; Chen, P. #
Magn. Reson. Chem. 2017, 55, 210-213.
“Application of a Computer-assisted Structure Elucidation Program for the Structural Determination of a New Terpenoid Aldehyde with an Unusual Skeleton.”
1. Mazzola, E. P.; # Gutierrez, O. #; Fraenkel, G. A.; Chow, A.; Doyle, M. P.; Mandler, M.; Dykstra, R.; Garg, D.; Ridge, C. D.
Concepts in Mag. Res. 2016, 45A:e21424.
“Unusually Large Scalar Coupling Between Geminal Protons in a Saturated Pyrimidine.”
Mentored Research
27. Gutierrez, O.; Hendrick, C. E.; Kozlowski, M. C.
Org. Lett. 2018, 20, 6539-6543.
Divergent Reactivity in Pd-Catalyzed [3,3]-Sigmatropic Rearrangement of Allyloxy- and Propargyloxyindoles Revealed by Computation and Experiment
26. Kim, B.-S.; Gutierrez, O.; Kozlowski, M.; Walsh, P. J.
Adv. Synth. Catal. 2018, 360, 1426-1432.
“A Simple Procedure for the Synthesis of β -Hydroxyallenamides via Homoallenylation of Aldehydes.”
25. Li, M.; Gutierrez, O.; Berritt, S.; Pascual-Escudero, A.; Yeşilçimen. A.; Tang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso, E.; Kozlowski, M. C.; Walsh, J. P.
Nat. Chem. 2017. 9, 997-1004.
“Transition-Metal-Free Chemo- and Regioselective Vinylation of Azaallyls.”
24. 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.
J. Am. Chem. Soc. 2016, 138, 15473-15481.
“Sequential C–H Arylation and Enantioselective Hydrogenation Enables Ideal Asymmetric Entry to the Indenopiperidine Core of an 11β-HSD-1 Inhibitor.”
23. 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.
Chem. Sci. 2016, 7, 5581-5586.
“Nickel-catalyzed C-3 direct arylation of pyridinium ions for the synthesis of 1-azafluorenes.”
22. Patel, A.; Chen, Z.; Yang, Z.; Gutierrez, O.; Liu, H.-v.; Houk, K. N.; Singleton, D. A.
J. Am. Chem. Soc. 2016, 138, 3631-3634.
“Dynamically Complex Enzyme-Catalyzed [6+4] and [4+2].”
21. Harrison, G. J.; Gutierrez, O.; Jana, N.; Driver, T.; Tantillo, D. J.
J. Am. Chem. Soc. 2016, 138, 487-490.
“Mechanism of R2(II)-Catalyzed Indole Formation—The Catalyst Does Not Control Product Selectivity.”
20. Wanner, B.; Kreituss, I.; Gutierrez, O.; Kozlowski, M. C.; Bode, J. W.
J. Am. Chem. Soc. 2015, 137, 11491-11497.
“Catalytic Kinetic Resolution of Disubstituted Piperidines by Enantioselective Acylation: Synthetic Utility and Mechanistic Insights.”
19. Gutierrez, O.; Tellis, J. C.; Primer, D. N.; Molander, G. A.; Kozlowski, M. C.
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.”
18. Gutierrez, O.; Dattatray, M.; Dwivedi, M.; Gudimalla, N.; Chandrashekar, E. R. R.; Vilas, D. H.; Bhattacharya, A.; Bandichhor, R.; Kozlowski, M. C.
Org. Lett. 2015, 17, 1742-1745.
“Development and Origin of Diastereoselectivity of a Practical and Asymmetric Route to Sitagliptin and Derivatives.”
17. Raffier, L.; Gutierrez, O.; Stanton, G. R.; Kozlowski, M. C.; Walsh, P. J. Organometallics, 2014, 33, 5371-5377.
“Alkenes as Chelating Groups in Diastereoselective Additions of Organometallics to Ketones.”
16. Allen, S. E.; Hsieh, S.-Y.; Gutierrez, O.; Bode, J. W.; Kozlowksi, M. C.
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.”
15. Williams, D. R.; Atwater, B, A.; Ke, P.; Gutierrez, O.; Tantillo, D. J.
Org. Lett. 2014, 16, 468-471.
“Stereocontrol in Asymmetric SE’ Reactions of γ-Substituted α,β-Unsaturated Aldehydes.”
14. Chen, M. Z.; Gutierrez, O.; Smith III, A. B.
Angew. Chem. Int. Ed. 2013, 53, 1279-1282.
“Through-Bond/Through-Space Anion Relay Chemistry Exploiting Vinylepoxides as Bifunctional Linchpins.”
13. Gutierrez, O.; Strick, B, F.; Thomson, R. J.; Tantillo, D. J.
Chem. Sci. 2013, 4, 3997-4003.
“Mechanism of Triflimide-Catalyzed [3,3]-Sigmatropic Rearrangements of N-Allylhydrazones – Predictions and Experimental Validation.”
12. Gutierrez, O.; Harrison, J. G.; Felix, R. J.; Guzman, F. C.; Gagné, M. R.; Tantillo, D. J. 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.”
11. Felix, R. J.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
J. Org. Chem. 2013, 78, 5685-5690.
“Gold(I)-Catalyzed Formation of Bicyclo[4.2.0]oct-1-enes.”
39. Dickstein, J. S.; Curto, J. M.; Gutierrez, O.; Mulrooney, C. A.; Kozlowski, M. C.
J. Org. Chem. 2013, 78, 4744-4761.
“Mild Aromatic Palladium-Catalyzed Protodecarboxylation: Kinetic Assessment of the Decarboxylative Palladation and the Protodepalladation Steps.”
10. Gutierrez, O.; Tantillo, D. J.
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.”
9. Gutierrez, O.; Harrison, J. G.; Pemberton, R. P.; Tantillo, D. J.
Chem. Eur. J. 2012, 18, 11029-11035.
"Reexamining the Mechanisms of Competing [3,3] and [3,5] Sigmatropic Shifts of 1,3,7-Octatriene."
8. Liu, R.; Gutierrez, O.; Tantillo, D. J.; Aubé, J.
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."
7. Laulhe, S.; Bogdanov, B.; Johannes, L. M.; Gutierrez, O.; Harrison, J. G.; Tantillo, D. J.; Zhang, X.; Nantz, M. H.
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."
6. Felix, R. J.; Weber, D.; Gutierrez, O.; Tantillo, D. J.; Gagné, M. R.
Nat. Chem. 2012, 4, 405-409.
"A Au-Catalyzed Enantioselective Cope Rearrangement of Achiral 1,5- Dienes."
5. Gutierrez, O.; Aubé, J.; Tantillo, D. J.
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.”
4. Gutierrez, O.; Tantillo, D. J.
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.”
3. Jung, M E.; Zhang, T.-H.; Lui, R. M.; Gutierrez, O.; Houk, K. N.
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.”
2. Um, J. M.; Gutierrez, O.; Schoenebeck, F.; Houk, K. N.; MacMillan. D. W. C.
J. Am. Chem. Soc. 2010, 132, 6001-6005.
“Nature of Intermediates in Organo-SOMO Catalysis of α-Arylation of Aldehydes.”
1. Gutierrez, O.; Iafe, R.; Houk, K. N.
Org. Lett. 2009, 11, 4298-4301.
“Origin of Stereoselectivity in the Imidazolidinone-Catalyzed Reductions of Cyclic α, β- Unsaturated Ketones.”