Houk, Kendall N.

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Distinguished Professor
Saul Winstein Chair
Chemical Biology
Theoretical Chemistry

Contact Information

Molecular Sciences Building 5505B
(310) 206-0515
Molecular Sciences Building 5240, 5440
(310) 825-0269

Short Biography

Professor Houk received his A.B., M.S., and Ph.D. degrees at Harvard University. He began his academic career at Louisiana State University in 1968, then taught at Princeton (Visiting Professor, 1975-1976) and Pittsburgh (1980-1986) before coming to UCLA in 1986. He was Director of the Chemistry Division at the National Science Foundation (1988-1990) and is currently Director of the Chemistry-Biology Interface Training Program at UCLA.


K. N. Houk was born in Nashville, Tennessee in 1943. He received his A.B. (1964), M.S. (1966), and Ph.D. (1968) degrees at Harvard, working with R. A. Olofson as an undergraduate and R. B. Woodward as a graduate student in the area of experimental tests of orbital symmetry selection rules. In 1968, he joined the faculty at Louisiana State University, becoming Professor in 1976. He has also been a Visiting Professor at Princeton. In 1980, he moved to the University of Pittsburgh, and in 1986, he moved to UCLA, becoming a Distinguished Professor in 1987. He has served on the Advisory Boards of the Chemistry Division of the National Science Foundation, the Petroleum Research Fund, a variety of journals, including Accounts of Chemical Research, the Journal of the American Chemical Society, the Journal of Organic Chemistry, Chemical and Engineering News, the Journal of Computational Chemistry, Chemistry-A European Journal, and the Journal of Chemical Theory and Computation. He was a member of the NIH Medicinal Chemistry Study Section and the NRC Board of Chemical Sciences and Technology. From 1988-1990, he was Director of the Chemistry Division of the National Science Foundation. He was Chairman of the UCLA Department of Chemistry and Biochemistry from 1991-1994 and was Chair of the AAAS Chemistry Section in 2005. He is a Fellow of the American Academy of Arts and Sciences, the American Association for the Advancement of Science, and of the World Association of Theoretical and Computational Chemists (new name of WATOC). He was co-chair, with Professor Cynthia Friend of Harvard, of a NSF-NIH-DOE-sponsored Workshop on Building Strong Academic Chemistry Departments Through Gender Equity in 2006. He currently is the Director of the UCLA Chemistry-Biology Interface Training Program and Senior Editor of Accounts of Chemical Research . He is a member of the NIH SBC-A Study Section and was Chair for 2007-2008. On July 1, 2009, he becomes the Saul Winstein Chair of Organic Chemistry at UCLA. He has published more than 750 articles in refereed journals, is among the 100 most-cited chemists, and is an avid runner, biker, and swimmer.

Research Interest

Professor Houk is an authority on theoretical and computational organic chemistry, and his group is involved in developments of rules to understand reactivity, computer modeling of complex organic reactions, and experimental tests of the predictions of theory. Among current interests are the modeling and design of enzyme-catalyzed reactions, the quantitative modelling of asymmetric reactions used in synthesis, the prediction of properties of materials and nanoscale devices and the molecular dynamics of organic reactions. His group is involved in collaborations all over the world.

Honors & Awards

Computers in Chemical and Pharmaceutical Research ACS Award for Computers in Chemistry and Pharmaceutical Research
American Academy of Arts and Sciences American Academy of Arts and Sciences
Japanese Society for the Promotion of Science Fellow of the JSPS
Hebrew University, Jerusalem Israel Lise Meitner Lecturer
Technion, Israel Lady Davis Fellow
American Chemical Society Southern California Section Tolman Medal
World Association of Theoretical Organic Chemistry Schrodinger Medal
University of Canterbury, Christchurch, New Zealand Visiting Erskine Fellow
Herbert Newby McCoy Award, UCLA
James Flack Norris Award in Physical Organic Chemistry
Arthur C. Cope Scholar Award
Fellow of the American Association for the Advancement of Science
Akron Section of the American Chemical Society Award
Von Humboldt U.S. Senior Scientist Award
LSU Distinguished Research Master Award
Alfred P. Sloan Foundation Research Fellowship
Camille and Henry Dreyfus Teacher-Scholar Grant
American Association for the Advancement of Science
American Chemical Society
Chemical Society of London
International Society of Quantum Biology
Inter-American Photochemical Society
International Academy of Quantum Moelcular Science


  • Elizabeth L. Noey, Yingdong Luo, Liming Zhang, and K. N. Houk:
    "Mechanism of Gold(I)-Catalyzed Rearrangements of Acetylenic Amine-N-Oxides: Computational Investigations Lead to a New Mechanism Confirmed by Experiment,"
    J. Am. Chem. Soc., 134, 1078-1084 (2012). (PDF)
  • Yu Lan, Rick L. Danheiser, and K. N. Houk:
    "Why Nature Eschews the Concerted [2 + 2 + 2] Cycloaddition of a Nonconjugated Cyanodiyne. Computational Study of a Pyridine Synthesis Involving an Ene-Diels-Alder-Bimolecular Hydrogen Transfer Mechanism,"
    J.Org. Chem., 77, 1533-1538 (2012). (PDF)
  • Elizabeth H. Krenske, Edwin C. Davison, Ian T. Forbes, Jacqueline A. Warner, Adrian L. Smith, Andrew B. Holmes, and K. N. Houk:
    "Reverse Cope Elimination of Hydroxylamines and Alkenes of Alkynes: Theoretical Investigation of Tether Length and Substituent Effects,"
    J. Am. Chem. Soc., 134, 2434-2441 (2012). (PDF)
  • Kinya Hotta, Xi Chen, Robert S. Paton, Atsushi Minami, Hao Li, Kunchithapadam Swaminathan, Irimpan I. Mathews, Kenji Watanabe, Hideaki Oikawa, Kendall N. Houk, and Chu-Young Kim:
    "Enzymatic Catalysis of Anti-Baldwin Ring Closure in Polyether Biosynthesis," Nature, 483, 355-359 (2012). (PDF)
  • Heidi K. Privett, Gert Kiss, Toni M. Lee, Rebecca Blomberg, Roberto A. Chica, Leonard M. Thomas, Donald Hilvert, Kendall N. Houk, and Stephen L. Mayo:
    "Iterative Approach to Computational Enzyme Design,"
    Proc. Natl. Acad. Sci., 109, 3790-3795 (2012). (PDF)
  • Peng Liu, Xiufang Xu, Xiaofei Dong, Benjamin K. Keitz, Myles B. Herbert, Robert H. Grubbs, and K. N. Houk:
    "Z-Selectivity in Olefin Metathesis with Chelated Ru Catalysts: Computational Studies of Mechanism and Selectivity,"
    J. Am. Chem. Soc., 134, 1464-1467 (2012). (PDF)
  • Andrew R. Bogdan, Steven V. Jerome, K. N. Houk, and Keith James: "Strained Cyclophane Macrocycles: Impact of Progressive Ring Size Reduction on Synthesis and Structure,"
    J. Am. Chem. Soc., 134, 2127-2138 (2012). (PDF)
  • Omid Khakshoor, Steven E. Wheeler, K. N. Houk, and Eric T. Kool: "Measurement and Theory of Hydrogen Bonding Contribution to Isosteric DNA Base Pairs,"
    J. Am. Chem. Soc., 134, 3154-3163 (2012). (PDF)
  • Yu-Hong Lam, K. N. Houk, Ulf Scheffler, and Rainer Mahrwald: "Stereoselectivities of Histidine-Catalyzed Asymmetric Aldol Additions and Contrasts with Proline Catalysis: A Quantum Mechanical Analysis,"
    J. Am. Chem. Soc., 134, 6286-6295 (2012). (PDF)
  • Myles B. Herbert, Yu Lan, Benjamin Keith Keitz, Peng Liu, Koji Endo, Michael W. Day, K. N. Houk, and Robert Howard Grubbs:
    "Decomposition Pathways of Z-Selective Ruthenium Metathesis Catalysts,"
    J. Am. Chem. Soc., 134, 7861-7866 (2012). (PDF)
  • Yu Lan, Peng Liu, Stephen G. Newman, Mark Lautens, and K. N. Houk: "Theoretical Study of Pd(0)-Catalyzed Carbohalogenation of Alkenes: Mechanism and Origins of Reactivities and Selectivities in Alkyl Halide Reductive Elimination from Pd(II) Species,"
    Chem. Sci., 3, 1987-1995 (2012). (PDF)
  • Carlos Aleman, Oscar Bertran, K. N. Houk, Anne Buyle Padias, and Henry K. Hall:
    "Thermodynamic and Stereochemical Aspects of the Polymerizability of Glycolide and Lactide,"
    Theor. Chem. Acc., 131, 1133-1142 (2012). (PDF)
  • Pankaj Jain, Hao Wang, Kendall N. Houk, and Jon C. Antilla:
    "Bronsted Acid Catalyzed Asymmetric Propargylation of Aldehydes,"
    Angew. Chem. Int. Ed., 51, 1391-1394 (2012). (PDF)
  • Daniel A. DiRocco, Elizabeth L. Noey, K. N. Houk, and Tomislav Rovis: "Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst,"
    Angew. Chem. Int. Ed., 51, 2391-2394 (2012). (PDF)
  • Adam E. Goetz, Sarah M. Bronner, Jordan D. Cisneros, Joshua M. Melamed, Robert S. Paton, K. N. Houk, and Neil K. Garg:
    "An Efficient Computational Model to Predict the Synthetic Utility of Heterocyclic Arynes,"
    Angew. Chem. Int. Ed., 51, 2758-2762 (2012). (PDF)
  • Hung V. Pham, David B. C. Martin, Christopher D. Vanderwal, and K. N. Houk:
    "The Intramolecular Diels-Alder Reaction of Tryptamine-Derived Zincke Aldehydes Is a Stepwise Process," Chem. Sci., 3 1650-1655 (2012). (PDF)
  • Qingquan Zhao, Yu-hong Lam, Mahboubeh Kheirabadi, Chongson Xu, K. N. Houk, and Christian E. Schafmeister:
    "Hydrophobic Stubstituent Effects on Proline Catalysis of Aldol Reactions in Water,"
    J. Org. Chem., 77, 4784-4792 (2012) (PDF)
  • Chelsea G. Gordon, Joel L. Mackey, John C. Jewett, Ellen M. Sletten, K. N. Houk, and Carolyn R. Bertozzi:
    "Reactivity of Biarylazacyclooctynones in Copper-Free Click Chemistry,"
    J. Am. Chem. Soc., 134, 9199-9208 (2012). (PDF)
  • Elizabeth H. Krenske, Emma W. Perry, Steven V. Jerome, Thomas J. Maimone, Phil S. Baran, and K. N. Houk:
    "Why a Proximity-Induced Diels-Alder Reaction Is So Fast,"
    Org. Lett., 14, 3016-3019 (2012). (PDF)
  • C. Avery Sader and K. N. Houk:
    "A Theoretical Study of Cyclohexyne Addition to Carbonyl-C alpha Bonds: Allowed and Forbidden Electrocyclic and Nonpericyclic Ring-Openings of Strained Cyclobutenes,"
    J. Org. Chem., 77, 4939-4948 (2012). (PDF)
  • Ryan J. Marcheschi, Han Li, Kechun Zhang, Elizabeth L. Noey, Seonah Kim, Asha Chaubey, K. N. Houk, and James C. Liao:
    "A Synthetic Recursive
    Pathway for Carbon Chain Elongation," ACS Chem. Biol., 7, 689-697 (2012). (PDF)
  • Elizabeth A. Felnagle, Asha Chaubey, Elizabeth L. Noey, Kendall N. Houk, and James C. Liao:
    "Engineering Synthetic Recursive Pathways to Generate Non-Natural Small Molecules,"
    Nature Chem. Biol., 8, 518-526 (2012). (PDF)
  • Geoffrey R. Nosrati and K. N. Houk:
    "SABER: A Computational Method for Identifying Active Sides for New Reactions,"
    Protein Science, 21, 697-706 (2012). (PDF)
  • Ana Bellomo, Nihan Celebi-Olcum, Xiaodong Bu, Nelo Rivera, Rebecca T. Ruck, Christopher J. Welch, Kendall N. Houk, and Spencer D. Dreher: "Rapid Catalyst Identification for the Synthesis of the Pyrimidinone Core of HIV Integrase Inhibitors,"
    Angew. Chem. Int. Ed., 51, 6912-6915 (2012). (PDF)
  • Xiufang Xu, Peng Liu, Adam Leser, Lauren E. Sirois, Paul A. Wender, and K. N. Houk:
    "Ligand Effects on Rates and Regioselectivities of Rh(I) Catalyzed (5+2) Cycloadditions: A Computational Study of Cyclooctadiene and Dinaphthocyclooctatetraene as Ligands,"
    J. Am. Chem. Soc., 134, 11012-11025 (2012). (PDF)
  • Peng Liu, Xing Yang, Vladimir B. Birman, and K. N. Houk:
    "Origin of Enantioselectivity in Benzotetramisole-Catalyzed Dynamic Kinetic Resolution of Azlactones,"
    Org. Lett., 14, 3288-3291 (2012). (PDF)
  • Elizabeth H. Krenske, Sesil Agopcan, Viktorya Aviyente, K. N. Houk, Brian A. Johnson, and Andrew B. Holmes:
    "Causation in a Cascade: The Origins of Selectivities in Intramolecular Nitrone Cycloadditions,"
    J. Am. Chem. Soc., 134, 12010-12015 (2012). (PDF)
  • Martin J. Schnermann, Nicholas L. Untiedt, Gonzalo Jimenez-Oses, Kendall N. Houk, and Larry E. Overman:
    "Forming Tertiary Organolithiums and Organocuprates from Nitrile Precursors and their Bimolecular Reactions with Carbon Electrophiles to Form Quaternary Carbon Stereocenters,"
    Angew. Chem. Int. Ed., 51, 9581-9586 (2012). (PDF)
  • Xing Yang, Peng Liu, K. N. Houk, and Vladimir B. Birman: "Manifestation of Felkin-Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids," Angew. Chem. Int. Ed., 51, 9638-9642 (2012). (PDF)
  • Ramesh Giri, Peng Liu, Yu Lan, K. N. Houk, and Jin-Quan Yu: "Understanding Reactivity and Stereoselectivity in Palladium-Catalyzed Diastereoselective sp3 C-H Bond Activation: Intermediate Characterization and Computational Studies,"
    J. Am. Chem. Soc., 134, 14118-14126 (2012). (PDF)
  • Florian Richter, Rebecca Blomberg, Sagar D. Khare, Gert Kiss, Alexandre P. Kuzin, Adam J. T. Smith, Jasmine Gallaher, Zbigniew Pianowski, Roger C. Helgeson, Alexej Grjasnow, Rong Xiao, Jayarraman Seetharaman, Min Su, Sergey Vorobiev, Scott Lew, Farhad Forouhar, Gregory J. Kornhaber, John F. Hunt, Gaetano T. Montelione, Liang Tong, K. N. Houk, Donald Hilvert, and David Baker:
    "Computational Design of Catalytic Dyads and Oxyanion Holes for Ester Hydrolysis,"
    J. Am. Chem. Soc., 134, 16197-19206 (2012). (PDF)
  • Xing Yang, Valentina D. Bumbu, Peng Liu, Ximin Li, Hui Jiang, Eric W. Uffman, Lei Guo, Wei Zhang, Xuntian Jiang, K. N. Houk, and Vladimir B. Birman:
    "Catalytic, Enantioselective N-Acylation of Lactams and Thiolactams Using Amidine-Based Catalysts,"
    J. Am. Chem. Soc., 134, 17605-17612 (2012). (PDF)
  • Kersey Black, Peng Liu, Lai Xu, Charles Doubleday, and Kendall N. Houk:
    "Inaugural Article: Dynamics, Transition States, and Timing of Bond Formation in Diels-Alder Reactions,"
    Proc. Natl. Acad. Sci. USA, 109, 12860-12865 (2012). (PDF)
  • Hao Wang, Philipp Kohler, Larry E. Overman, and K. N. Houk:
    "Origins of Stereoselectivities of Dihydroxylations of cis-Bicyclo[3.3.0]octenes,"
    J. Am. Chem. Soc., 134, 16054-16058 (2012). (PDF)
  • Yong Liang, Joel L. Mackey, Steven A. Lopez, Fang Liu, and K. N. Houk:
    "Control and Design of Mutual Orthogonality in Bioorthogonal Cycloadditions,"
    J. Am. Chem. Soc., 134, 17904-17907 (2012). (PDF)
  • Mahboubeh Kheirabadi, Nihan Celebi-Olcum, Matthew F. L. Parker, Qingquan Zhao, Gert Kiss, K. N. Houk, and Christian E. Schafmeister: "Spiroligozymes for Transesterifications: Design and Relationship of Structure to Activity,"
    J. Am. Chem. Soc., 134, 18345-18353 (2012). (PDF)
  • Gregg A. Barcan, Ashay Patel, K. N. Houk, and Ohyun Kwon:
    "A Torquoselective 6pi Electrocyclization Approach to Reserpine Alkaloids,"
    Org. Lett., 14, 5388-5381 (2012). (PDF)
  • Olga Khersonsky, Gert Kiss, Daniela Rothlisberger, Orly Dym, Shira Albeck, Kendall N. Houk, David Baker, and Dan S. Tawfik:
    "Bridging the Gaps in Design Methodologies by Evolutionary Optimization of the Stability and Proficiency of Designed Kemp Eliminase KE59," Proc. Natl. Acad. Sci. USA, 109, 10358-10363 (2012). (PDF)
  • Yu-hong Lam, Kendall N. Houk, Janine Cossy, Domingo Gomez Pardo, and Anne Cochi:
    "Fluorine as a Regiocontrol Element in the Ring Opening of Bicyclic Aziridiniums,"
    Helv. Chim. Acta, 95, 2265-2277 (2012). (PDF)
  • Marinus A. Bigi, Peng Liu, Lufeng Zou, K. N. Houk, and M. Christina White:
    "Cafestol to Tricalysiolide B and Oxidized Analogues: Biosynthetic and Derivatization Studies Using Non-heme Iron Catalyst Fe(PDP),"
    Synlett, 23, 2768-2772 (2012). (PDF)
  • Ricardo A. Matute and K. N. Houk:
    "The Triplet Surface of the Zimmerman Di-pi-Methane Rearrangement of Dibenzobarrelene," Angew. Chem. Int. Ed., 51, 13097-13100 (2012). (PDF)
  • Hiroshi Miyazaki, Myles B. Herbert, Peng Liu, Xiaofei Dong, Xiufang Xu, Benjamin K. Keitz, Thay Ung, Garik Mkrtumya, K. N. Houk, and Robert H. Grubbs:
    "Z-Selective Ethenolysis with a Ruthenium Metathesis Catalyst: Experiment and Theory,"
    J. Am. Chem. Soc., 135, 5848-5858 (2013). (PDF)
  • Hao Wang, Fang Liu, Roger C. Helgeson, Kendall N. Houk:
    "Reversible Photochemically Gated Transformation of a Hermicarcerand to a Carcerand,"
    Angew. Chem. Int. Ed., 52, 655-659 (2012). (PDF)
  • Sarah M. Bronner, Joel L. Mackey, K. N. Houk, and Neil K. Garg: "Steric Effects Compete with Aryne Distortion to Control Regioselectivities of Nucleophilic Additions to 3-Silylarynes,"
    J. Am. Chem. Soc., 134, 13966-13969 (2012). (PDF)
  • Geoffrey R. Nosrati and K. N. Houk:
    "Using Catalytic Atom Maps to Predict the Catalytic Functions Present in Enzyme Active Sites," Biochem., 51, 7321-7329 (2012). (PDF)
  • Andrej Petric, Scott A. Johnson, Hung V. Pham, Ying Li, Simon Ceh, Amalija Golobic, Eric D. Agdeppa, Gerald Timbol, Jie Liu, Gyochang Keum, Nagichettiar Satyamurthy, Vladimir Kepe, Kendall N. Houk, and Jorge R. Barrio:
    "Dicyanovinylnaphthalenes for Neuroimaging of Amyloids and Relationships of Electronic Structures and Geometries to Binding Affinities,"
    Proc. Natl. Acad. Sci. USA, 109, 16492-16497 (2012). Correction: Proc. Natl. Acad. Sci. USA, 110, 5269 (2013). (PDF)
  • Arne Dieckmann and K. N. Houk:
    "Elucidation of Strong Cooperative Effects Caused by Dispersion Interactions in a Recognition-Mediated Diels-Alder Reaction,"
    J. Chem. Theory Comput., 8, 5064-5071 (2012). (PDF)
  • Huiliang Wang, Jianguo Mei, Peng Liu, Kristin Schmidt, Gonzalo Jimenez-Oses, Silvia Osuna, Lei Fang, Christopher J. Tassone, Arjan Pieter Zoombelt, Anatoliy N. Sokolov, Kendall N. Houk, Michael F. Toney, and Zhenan Bao:
    "Scalable and Selective Dispersion of Semiconducting Arc-Discharged Carbon Nanotubes by Dithiafulvalene/Thiophene Copolymers for Thin Film Transistors," ACS Nano, 7, 2659-2668 (2013). (PDF)
  • Hongkun Lin, Wenbo Pei, Hao Wang, Kendall N. Houk, and Isaac J. Krauss:
    "Enantioselective Homocrotylboration of Aliphatic Aldehydes,"
    J. Am. Chem. Soc., 135, 82-85 (2013). (PDF)
  • Xin Hong, Peng Liu, and K. N. Houk:
    "Mechanism and Origins of Ligand-Controlled Selectivities in [Ni(NHC)]-Catalyzed Intramolecular (5+2) Cycloadditions and Homo-Ene Reactions: A Theoretical Study,"
    J. Am. Chem. Soc., 135, 1456-1462 (2013). (PDF)
  • Arne Dieckmann, Martin Breugst, and K. N. Houk:
    "Zwitterions and Unobserved Intermediates in Organocatalytic Diels-Alder Reactions of Linear and Cross-Conjugated Trienamines,"
    J. Am. Chem. Soc., 135, 3237-3242 (2013). (PDF)
  • Hao Wang, Pankaj Jain, Jon C. Antilla, and K. N. Houk:
    "Origins of Stereoselectivities in Chiral Phosphoric Acid Catalyzed Allylborations and Propargylations of Aldehydes,"
    J. Org. Chem., 78, 1208-1215 (2013). (PDF)
  • Steven A. Lopez, Morton E. Munk, and K. N. Houk:
    "Mechanisms and Transition States of 1,3-Dipolar Cycloadditions of Phenyl Azide with Enamines: A Computational Analysis,"
    J. Org. Chem., 78, 1576-1582 (2013). Correction: J. Org. Chem., 78, 5115-5115 (2013). (PDF)
  • Yunfei Du, Elizabeth H. Krenske, Jennifer E. Antoline, Andrew G. Lohse, K. N. Houk, and Richard P. Hsung:
    "Control of Regioselectivity and Stereoselectivity in (4+3) Cycloadditions of Chiral Oxyallyls with Unsymmetrically Disubsituted Furans,"
    J. Org. Chem., 78, 1753-1759 (2013). (PDF)
  • Steven A. Lopez and K. N. Houk:
    "Alkene Distortion Energies and Torsional Effects Control Reactivities and Stereoselectivities of Azide Cycloadditions to Norbornene and Substituted Norbornenes," J. Org. Chem., 78, 1778-1783 (2013). (PDF)
  • Christopher J. Rosenker, Elizabeth H. Krenske, K. N. Houk, and Peter Wipf:
    "Influence of Base and Structure in the Reversible Covalent Conjugate Addition of Thiol to Polycyclic Enone Scaffolds," Org. Lett., 15, 1076-1079 (2013). (PDF)
  • Elizabeth H. Krenske and K. N. Houk:
    "Aromatic Interactions as Control Elements in Stereoselective Organic Reactions,"
    Acc. Chem. Res., 46, 979-989 (2013). (PDF)
  • Gert Kiss, Vijay S. Pande, and K. N. Houk:
    "Molecular Dynamics Simulations for the Ranking, Evaluation, and Refinement of Computationally Designed Proteins,"
    Methods in Enzymology, 523, 145-170 (2013). (PDF)
  • Sinisa Bjelic, Lucas G. Nivon, Nihan Celebi-Olcum, Gert Kiss, Carolyn F. Rosewall, Helena M. Lovick, Erica L. Ingalls, Jasmine Lynn Gallaher, Jayaraman Seetharaman, Scott Lew, Gaetano Thomas Montelione, John Francis Hunt, Forrest Edwin Michael, K. N. Houk, and David Baker:
    "Computational Design of Enone-Binding Proteins with Catalytic Activity for the Morita-Baylis-Hillman Reaction," ACS Chem. Biol., 8 749-757 (2013). (PDF)
  • Elizabeth H. Krenske, Shuzhong He, Jian Huang, Yunfei Du, K. N. Houk, and Richard P. Hsung:
    "Intramolecular Oxyallyl-Carbonyl (3 + 2) Cycloadditions,"
    J. Am. Chem. Soc., 135, 5242-5245 (2013). (PDF)
  • Ashay Patel, Gregg A. Barcan, Ohyun Kwon, and K. N. Houk:
    "Origins of 1,6-Stereoinduction in Torquoselective 6 pi Electrocyclizations,"
    J. Am. Chem. Soc., 135, 4878-4883 (2013). (PDF)
  • Yvonne Schmidt, Jonathan K. Lam, Hung V. Pham, K. N. Houk, and Christopher D. Vanderwal:
    "Studies on the Himbert Intramolecular Arene/Allene Diels-Alder Cycloaddition. Mechanistic Studies and Expansion of Scope to All-Carbon Tethers,"
    J. Am. Chem. Soc., 135, 7339-7348 (2013). (PDF)
  • Silvia Osuna, Seonah Kim, Guillaume Bollot, and Kendall N. Houk: "Aromatic Claisen Rearrangements of O-Prenylated Tyrosine and Model Prenyl Aryl Ethers: Computational Study of the Role of Water on Acceleration of Claisen Rearrangements,"
    Eur. J. Org. Chem., 2823-2831 (2013). (PDF)
  • Xin Hong, Barry M. Trost, and K. N. Houk:
    "Mechanism and Origins of Selectivity in Ru(II)-Catalyzed Intramolecular (5+2) Cycloadditions and Ene Reactions of Vinylcyclopropanes and Alkynes from Density Functional Theory,"
    J. Am. Chem. Soc., 135, 6588-6600 (2013). (PDF)
  • Lufeng Zou, Robert S. Paton, Albert Eschenmoser, Timothy R. Newhouse, Phil S. Baran, and K. N. Houk:
    "Enhanced Reactivity in Dioxirane C-H Oxidations via Strain Release: A Computational and Experimental Study,"
    J. Org. Chem., 78, 4037-4048 (2013). (PDF)
  • Tom Mejuch, Noga Gilboa, Eric Gayon, Hao Wang, K. N. Houk, and Ilan Marek:
    "Axial Preferences in Allylation Reactions via the Zimmerman-Traxler Transition State,"
    Acc. Chem. Res., 46, 1659-1669 (2013). (PDF)
  • Shudan Bian, Amy M. Scott, Yang Cao, Yong Liang, Silvia Osuna, K. N. Houk, and Adam B. Braunschweig:
    "Covalently Patterned Graphene Surfaces by a Force Accelerated Diels-Alder Reaction,"
    J. Am. Chem. Soc., 135, 9240-9243 (2013). (PDF)
  • Gert Kiss, Nihan Celebi-Olcum, Rocco Moretti, David Baker, and K. N. Houk:
    "Computational Enzyme Design,"
    Angew. Chem. Int. Ed., 52, 5700-5725 (2013). (PDF)
  • Xiufang Xu, Peng Liu, Xing-Zhong Shu, Weiping Tang, and K. N. Houk: "Rh-Catalyzed (5+2) Cycloadditions of 3-Acyloxy-1,4-enynes and Alkynes: Computational Study of Mechanism, Reactivity, and Regioselectivity,"
    J. Am. Chem. Soc., 135, 9271-9274 (2013). (PDF)
  • Changxia Yuan, Yong Liang, Taylor Hernandez, Adrian Berriochoa, Kendall N. Houk, and Dionicio Siegel:
    "Metal-Free Oxidation of Aromatic Carbon-Hydrogen Bonds Through a Reverse-Reound Mechanism," Nature, 499, 192-196 (2013). (PDF)
  • Natalie C. James, Joann M. Um, Anne B. Padias, H. K. Hall Jr., and K. N. Houk:
    "Computational Investigation of the Competition Between the Concerted Diels-Alder Reaction and Formation of Diradicals in Reactions of Acrylonitrile with Nonpolar Dienes,"
    J. Org. Chem., 78, 6582- 6592 (2013). (PDF)
  • Arne Dieckmann and K. N. Houk:
    "Analysis of Supramolecular Complex Energetics in Artifical Replicators,"
    Chem. Sci., 4, 3591-3600 (2013). (PDF)
  • Xue Gao, Wei Jiang, Gonzalo Jimenez-Oses, Moon Seok Choi, Kendall N. Houk, Yi Tang, and Christopher T. Walsh:
    "An Iterative, Bimodular Nonribosomal Peptide Synthetase that Converts Anthranilate and Tryptophan into Tetracyclic Asperlicins,"
    Chem. & Biol., 20, 870-878 (2013). (PDF)
  • David N. Kamber, Lidia A. Nazarova, Yong Liang, Steven A. Lopez, David M. Patterson, Hui-Wen Shih, K. N. Houk, and Jennifer A. Prescher:
    "Isomeric Cyclopropenes Exhibit Unique Bioorthogonal Reactivities,"
    J. Am. Chem. Soc., 135, 13680-13683 (2013). (PDF)
  • Caroline Souris, Frederic Frebault, Ashay Patel, David Audisio, K. N. Houk, and Nuno Maulide:
    "Stereoselective Synthesis of Dienyl-Carboxylate Building Blocks: Formal Synthesis of Inthomycin C,"
    Org. Lett. 15, 3242-3245 (2013). (PDF)
  • Fang Liu, Robert S. Paton, Seonah Kim, Yong Liang, and K. N. Houk: "Diels-Alder Reactivities of Strained and Unstrained Cycloalkenes with Normal and Inverse-Electron-Dmand- Dienes: Activation Barriers and Distortion/Interaction Analysis,"
    J. Am. Chem. Soc., 135, 15642-15649 (2013). (PDF)
  • Jeffrey C. Holder, Lufeng Zou, Alexander N. Marziale, Peng Liu, Yu Lan, Michele Gatti, Kotaro Kikushima, K. N. Houk, and Brian M. Stoltz:
    "Mechanism and Enantioselectivity in Palladium-Catalyzed Conjugate Addition of Arylboronic Acids to beta-substituted Cyclic Enones: Insights from Computation and Experiment,"
    J. Am. Chem. Soc., 135, 14996-15007 (2013). (PDF)
  • Lei Fang, Peng Liu, Benjamin R. Sveinbjornsson, Sule Atahan-Evrenk, Koen Vandewal, Silvia Osuna, Gonzalo Jimenez-Oses, Supriya Shrestha, Gaurav Giri, Peng Wei, Alberto Salleo, Alan Aspuru-Guzik, Robert H. Grubbs, K. N. Houk, and Zhenan Bao:
    "Confined Organization of Fullerene Units Along High Polymer Chains,"
    J. Mater. Chem. C, 1, 5747-5755 (2013). (PDF)
  • Fang Liu, Hao Wang, and Kendall N. Houk:
    "Gating in Host-Guest Chemistry,"
    Current Organic Chemistry, 17, 1470-1480 (2013). (PDF)
  • Gonzalo Jimenez-Oses, Anthony J. Brockway, Jared T. Shaw, and K. N. Houk:
    "Mechanism of Alkoxy Groups Substitution by Grignard Reagents on Aromatic Rings and Experimental Verification of Theoretical Predictions of Anomalous Reactions,"
    J. Am. Chem. Soc., 135, 6633-6642 (2013). (PDF)
  • Martin Breugst, Albert Eschenmoser, and K. N. Houk:
    "Theoretical Exploration of the Mechanism of Riboflavin Formation from 6,7-Dimethyl-8-ribityllumazine: Nucleophilic Catalysis, Hydride Transfer, Hydrogen Atom Transfer, or Nucleophilic Addition?,"
    J. Am. Chem. Soc., 135, 6658-6668 (2013). (PDF)
  • Arne Dieckmann, Matthew T. Richers, Alena Yu Platonova, Chen Zhang, Daniel Seidel, and K. N. Houk:
    "Metal-Free alpha-Amination of Secondary Amines: Computational and Experimental Evidence for Azaquinone Methide and Azomethine Ylide Intermediates,"
    J. Org. Chem., 135, 4132-4144 (2013). (PDF)
  • Marie S. T. Morin, Daniel J. St-Cyr, Bruce Alan Arndtsen, Elizabeth H. Krenske, and K. N. Houk:
    "Modular Mesoionics: Understanding and Controlling Regioselectivity in 1,3-Dipolar Cycloaddtions of Munchnone Derivatives,"
    J. Am. Chem. Soc., 135, 17349-17358 (2013). (PDF)
  • Hao Wang and K. N. Houk:
    "&Torsional Control of Stereoselectivities in Electrophilic Additions and Cycloadditions to Alkenes,"
    Chem. Sci., 5, 462-470 (2014). (PDF)
  • Gregg M. Schwarzwalder, Sarah E. Steinhardt, Hung V. Pham, K. N. Houk, and Christopher D. Vanderwal:
    "Synthesis of the Tetracyclic Core of Exiguaquinol,"
    Org. Lett., 15, 6014-6017 (2013). (PDF)
  • Shiyu Zhang, Nihan Celebi-Olcun, Marie M. Melzer, K. N. Houk, and Timothy H. Warren:
    "Copper(I) Nitrosyls from Reacion of Copper (II) Thiolates with S-Nitrosothiols: Mechanism of NO Release from RSNOs at Cu,"
    J. Am. Chem. Soc., 135, 16746-16749 (2013). (PDF)
  • Yang Cao, Silvia Osuna, Yong Liang, Robert C. Haddon, and K. N. Houk: "Diels-Alder Reactions of Graphene: Computational Predictions of Products and Sites of Reaction,"
    J. Am. Chem. Soc., 135, 17643-17649 (2013). (PDF)
  • Arlene Russell and Kendall N. Houk:
    "Orville Chapman, 1932-2004, A Biographical Memoir,"
    Natl. Acad. Sci. Biographical Memoirs (2013). (PDF)
  • Xin Hong, Yong Liang, Allison K. Griffith, Tristan H. Lambert, and K. N. Houk:
    "Distortion-Accelerated Cycloadditions and Strain-Release-Promoted Cycloreversions in the Organocatalytic Carbonyl-Olefin Metathesis,"
    Chem. Sci., 5, 471-475 (2014). (PDF)
  • Yun-Fang Yang, Gui-Juan Cheng, Peng Liu, Dasheng Leow, Tian-Yu Sun, Ping Chen, Xinhao Zhang, Jin-Quan Yu, Yun-Dong Wu, and K. N. Houk: "Palladium-Catalyzed Meta-Selective C-H Bond Activation with a Nitrile-Containing Template: Computational Study on Mechanism and Origins of Selectivity,"
    J. Am. Chem. Soc., 136, 344-355 (2014). (PDF)
  • Jonathan K. Lam, Hung V. Pham, K. N. Houk, and Christopher D. Vanderwal:
    "Computation and Experiment Reveal That the Ring-Rearrangement Metathesis of Himbert Cycloadducts Can Be Subject to Kinetic or Thermodynamic Control,"
    J. Am. Chem. Soc., 135, 17585-17594 (2013). (PDF)
  • Elizabeth H. Krenske, Ashay Patel, and K. N. Houk:
    "Does Nature Click? Theoretical Prediction of an Enzyme-Catalyzed Transannular 1,3-Dipolar Cycloaddition in the Biosynthesis of Lycojaponicumins A and B,"
    J. Am. Chem. Soc., 135, 17638-17642 (2013). (PDF)
  • Silvia Osuna, Alpay Dermenici, Scott J. Miller, and K. N. Houk:
    "The Roles of Counterion and Water in a Stereoselective Cysteine-Catalyzed Rauhut-Currier Reaction: A Challenge for Computational Chemistry," Chem. Eur. J., 19, 14245-14253 (2013). (PDF)
  • Peter K. Dornan, Kevin G. M. Kou, K. N. Houk, and Vy M. Dong: "Dynamic Kinetic Resolution of Allylic Sulfoxides by Rh-Catalyzed Hydrogenation: A Combined Theoretical and Experimental Mechanistic Study,"
    J. Am. Chem. Soc., 136, 291-298 (2014). (PDF)
  • Matthew F. L. Parker, Silvia Osuna, Guillaume Bollot, Shivaiah Vaddypally, Michael J. Zdilla, K. N. Houk, and Christian E. Schafmeister:
    "Acceleration of an Aromatic Claisen Rearrangement via a Designed Spiroligozyme Catalyst that Mimics the Ketosteroid Isomerase Catalytic Dyad,"
    J. Am. Chem. Soc., 136, 3817-3827 (2014). (PDF)
  • C. Avery Sader and K. N. Houk:
    "Distortion/Interaction Analysis of the Reactivities and Selectivities of Halo- and Methoxy-Substituted Carbenes with Alkenes,"
    ARKIVOC, 2014 (iii), 170-183 (2014). (PDF)
  • Hung V. Pham, Robert S. Paton, Audrey G. Ross, Samuel J. Danishefsky, and K. N. Houk:
    "Intramolecular Diels-Alder Reactions of Cycloalkenones: Stereoselectivity, Lewis Acid Acceleration, and Halogen Substituent Effects,"
    J. Am. Chem. Soc., 136, 2397-2403 (2014). (PDF)
  • Denisse de Loera, Fang Liu, K. N. Houk, and Miguel A. Garcia-Garibay: "Aziridine Nitrogen Inversion by Dynamic NMR: Activation Parameters in a Fused Bicyclic Structure,"
    J. Org. Chem., 78, 11623-11636 (2013). (PDF)
  • Olivier Loiseleur, Jerome Cassayre, Dominique Leca, Francesca Gaggini, Susan N. Pieniazek, Jennifer A. R. Luft, and Kendall N. Houk:
    "Control of Hetero-Diels-Alder Stereoselectivity through Solvent Polarity and Bronsted or Lewis Acid Catalysis: Theory and Experiment,"
    Synlett, 24, 2446-2450 (2013). (PDF)
  • Martin Breugst, Rene Gree, and K. N. Houk:
    "Synergistic Effects between Lewis and Bronsted Acids: Application to the Prins Cyclization,"
    J. Org. Chem., 78, 9892-9897 (2013). (PDF)
  • Gonzalo Jimenez-Oses, Peng Liu, Ricardo A. Matute, and Kendall N. Houk:
    "Competition Between Concerted and Stepwise Dynamics in the Triplet Di-pi-Methane Rearrangement,"
    Angew. Chem. Int. Ed., 53, 8664-8667 (2014). (PDF)
  • Seoung-ryoung Choi, Martin Breugst, K. N. Houk, and C. Dale Poulter: "delta-Deuterium Isotope Effects as Probes for Transition State Structures of Isoprenoid Substrates,"
    J. Org. Chem., 79, 3572-3580 (2014). (PDF)
  • Matthew T. Richers, Martin Breugst, Alena Yu Platonova, Anja Ullrich, Arne Dieckmann, K. N. Houk, and Daniel Seidel:
    "Redox-Neutral alpha-Oxygenation of Amines: Reaction Development and Elucidation of the Mechanism,"
    J. Am. Chem. Soc., 136, 6123-6135 (2014). (PDF)
  • Jun Zhu, Yong Liang, Lijia Wang, Zhong-Bo Zheng, K. N. Houk, and Yong Tang:
    "Remote Ester Groups Switch Selectivity: Diastereodivergent Synthesis of Tetracyclic Spiroindolines,"
    J. Am. Chem. Soc., 136, 6900-6903 (2014). (PDF)
  • Aaron G. Green, Peng Liu, Craig A. Merlic, and K. N. Houk: "Distortion/Interaction Analysis Reveals the Origins of Selectivities in Iridium-Catalyzed C-H Borylation of Substituted Arenes and 5-Membered Heterocycles,"
    J. Am. Chem. Soc., 136, 4575-4583 (2014). (PDF)
  • Huiliang Wang, Ghada I. Koleilat, Peng Liu, Gonzalo Jimenez-Oses, Ying-Chih Lai, Michael Vosgueritchian, Ya Fang, Steve Park, Kendall N. Houk, and Zhenan Bao:
    "High-Yield-Sorting of Small-Diameter Carbon Nanotubes for Solar Cells and Transistors,"
    ACS Nano, 8, 2609-2617 (2014). (PDF)
  • Jun Yang, Yong Liang, Jolita Seckute, K. N. Houk, Neal K. Devaraj: "Synthesis and Reactivity Comparisons of 1-Methyl-3-Substituted Cyclopropene Mini-tags for Tetrazine Bioorthogonal Reactions," Chem. Eur. J., 20, 3365-3375 (2014). (PDF)
  • Xin Hong, Yong Liang, and K. N. Houk:
    "Mechanisms and Origins of Switchable Chemoselectivity of Ni-Catalyzed C(aryl)-O and C(acyl)-O Activation of Aryl Esters with Phosphone Ligands,"
    J. Am. Chem. Soc., 136, 2017-2025 (2014). (PDF)
  • Gui-Juan Cheng, Yun-Fang Yang, Peng Liu, Ping Chen, Tian-Yu Sun, Gang Li, Xinhao Zhang, K. N. Houk, Jin-Quan Yu, and Yun-Dong Wu:
    "Role of N-Acyl Amino Acid Ligands in Pd(II)-Catalyzed Remote C-H Activation of Tethered Arenes,"
    J. Am. Chem. Soc., 136, 894-897 (2014). (PDF)
  • Michael E. Jung, Gloria S. Lee, Hung V. Pham, and K. N. Houk: "Palladium Hydride Promoted Stereoselective Isomerization of Unactivated Di(exo)methylenes to Endocyclic Dienes,"
    Org. Lett., 16, 2382-2385 (2014). (PDF)
  • Jeffrey S. Cannon, Lufeng Zou, Peng Liu, Yu Lan, Daniel J. O’Leary, K. N. Houk, and Robert H. Grubbs:
    "Carboxylate-Assisted C(sp3)-H Activation in Olefin Metathesis-Relevant Ruthenium Complexes,"
    J. Am. Chem. Soc., 136, 6733-6743 (2014). (PDF)
  • Gabrielle J. Dugas, Yu-hong Lam, K. N. Houk, and Isaac J. Krauss: "Boron Carboxylate Catalysis of Homoallylboration,"
    J. Org. Chem., 79, 4277-4284 (2014). (PDF)
  • Gonzalo Jimenez-Oses, Silvia Osuna, Xue Gao, Michael R. Sawaya, Lynne Gilson, Steven J. Collier, Gjalt W. Huisman, Todd O. Yeates, Yi Tang, and K. N. Houk:
    "The Role of Distant Mutations and Allosteric Regulation on LovD Active Site Dynamics,"
    Nature Chem. Biol., 10, 431-436 (2014). (PDF)
  • Anh T. Tran, Peng Liu, K. N. Houk, and Kenneth M. Nicholas: "Regioselectivity in the Cu(I)-Catalyzed [4+2]-Cycloaddition of 2-Nitrosopyridine with Unsymmetrical Dienes,"
    J. Org. Chem., 79, 5617-5626 (2014). (PDF)
  • K. N. Houk:
    "Foreword: Applied Computational Chemistry," Chem. Soc. Rev., 43, 4905-4905 (2014). (PDF)
  • Claire L. Jarvis, Matthew T. Richers, Martin Breugst, K. N. Houk, and Daniel Seidel:
    "Redox-Neutral alpha-Sulfenylation of Secondary Amines: Ring-Fused N,S-Acetals,"
    Org. Lett., 16, 3556-3559 (2014). (PDF)
  • Steven Lopez and K. N. Houk:
    "Substituent Effects on Rates and Torquoselectivities of Electrocyclic Ring-Openings of N-Substituted 2-Azetines,"
    J. Org. Chem., 79, 6189-6195 (2014). (PDF)
  • Fang Liu, Roger C. Helgeson, and K. N. Houk:
    "Building on Cram's Legacy: Stimulated Gating in Hemicarcerands,"
    Acc. Chem. Res., 47, 2168-2176 (2014). (PDF)
  • Martin Breugst and K. N. Houk:
    "Computational Analysis of Cyclophane-Based Bisthiourea-Catalyzed Henry Reactions,"
    J. Org. Chem., 79, 6302-6309 (2014). (PDF)
  • Yu-hong Lam and K. N. Houk:
    "How Cinchona Alkaloid-Derived Primary Amines Control Asymmetric Electrophilic Fluorination of Cyclic Ketones,"
    J. Am. Chem. Soc., 136, 9556-9559 (2014). (PDF)
  • Xu Han, Shudan Bian, Yong Liang, K. N. Houk, and Adam B. Braunschweig:
    "Reactions in Elastomeric Nanoreactors Reveal the Role of Force on the Kinetics of the Huisgen Reaction on Surfaces,"
    J. Am. Chem. Soc., 136, 10553-10556 (2014). (PDF)
  • Yang Cao, Yong Liang, Lei Zhang, Silvia Osuna, Andra-Lisa M. Hoyt, Alajandro L. Briseno, and K. N. Houk:
    "Why Bistetracenes Are Much Less Reactive Than Pentacenes in Diels-Alder Reactions with Fullerenes,"
    J. Am. Chem. Soc., 136, 10743-10751 (2014). (PDF)
  • Xiao-Na Wang, Elizabeth H. Krenske, Ryne C. Johnston, K. N. Houk, and Richard P. Hsung:
    "Torquoselective Ring Opening of Fused Cyclobutenamides: Evidence for a Cis, Trans-Cyclooctadienone Intermediate,"
    J. Am. Chem. Soc., 136, 9802-9805 (2014). (PDF)
  • Hasnain A. Malik, Buck L. H. Taylor, John R. Kerrigan, Jonathan E. Grob, K. N. Houk, J. Du Bois, Lawrence G. Hamann, and Andrew W. Patterson:
    "Non-Directed Allylic C-H Acetoxylation in the Presence of Lewis Basic Hetercycles,"
    Chem. Sci., 5, 2352-2361 (2014). (PDF)
  • Youcai Hu, David Dietrich, Wei Xu, Ashay Patel, Justin A. J. Thuss, Jingjing Wang, Wen-Bind Yin, Kangjian Qiao, K. N. Houk, John C. Vederas, and Yi Tang:
    "A Carbonate-Forming Baeyer-Villiger Monooxygenase,"
    Nature Chem. Biol., 10, 552-554 (2014). (PDF)
  • Fang Liu, Yong Liang, and K. N. Houk:
    "Theoretical Elucidation of the Origins of Substituent and Strain Effects on the Rates of Diels-Alder Reactions of 1,2,4,5-Tetrazines,"
    J. Am. Chem. Soc., 136, 11483-11493 (2014). (PDF)
  • Xin Hong, Yong Liang, Matthias Brewwer, and K. N. Houk:
    "How Tethers Control the Chemo- and Regioselectivities of Intramolecular Cycloadditions between Aryl-1-aza-2-azoniaallenes and Alkenes,"
    Org. Lett., ASAP Article (2014). (PDF)
  • Steven A. Lopez, Melika Pourati, Hans Joachim Gais, and K. N. Houk: "How Torsional Effects Cause Attack at Sterically Crowded Concave Faces of Bicyclic Alkenes,"
    J. Org. Chem., Just Accepted Manuscript (2014). (PDF)