Houk, Kendall N.

Organic

Houk Kendall

Biography

K. N. Houk received his A.B., M.S., and Ph.D. degrees at Harvard, working with R. B. Woodward on experimental tests of orbital symmetry selection rules. In 1968, he joined the faculty at Louisiana State University, moved to the University of Pittsburgh in 1980, and to UCLA in 1986. 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.  He was the Saul Winstein Chair in Organic Chemistry from 2009-2021 and is now Distinguished Research Professor.

Professor Houk has been awarded the von Humboldt Foundation U.S. Senior Scientist Award in 1981, an Arthur C. Cope Scholar Award from the ACS in 1988, the 1991 ACS James Flack Norris Award in Physical Organic Chemistry, and the 1998 of the Schrödinger Medal of the World Association of Theoretical and Computational Chemists (WATOC). He was the Faculty Research Lecturer at UCLA, received the Bruylants Chair from the University of Louvain-la-Neuve in Belgium in 1998, and received an honorary doctorate (Dr. rer. nat. h. c.) from the University of Essen in Germany in 1999. He has been an Erskine Fellow in New Zealand, a Lady Davis Fellow at the Technion in Haifa, Israel, and a JSPS Fellow in Japan. He was named Honorary Professor at the University of Queensland, Brisbane, Australia, in 2014. He won the Tolman Medal of the Southern California Section of the ACS in 1999. He was elected to the American Academy of Arts and Sciences in 2002 and the International Academy of Quantum Molecular Sciences in 2003. He was the 2003 winner of the ACS Award for Computers in Chemical and Pharmaceutical Sciences. He is a Fellow of the AAAS, the ACS, and of the WATOC. He was awarded the Arthur C. Cope Award of the ACS in 2009, was elected a member of the National Academy of Sciences in 2010, became a Fellow of the Royal Society of Chemistry in 2012, and was awarded the Robert Robinson Award of the Royal Society of Chemistry in 2012. He received the UCLA Society of Postdoctoral Scholars Mentoring Award and the UCLA Glenn T. Seaborg Medal in 2013. He received the UCLA 2019-2020 Edward A. Dickson Award. He received the 2021 Roger Adams Award of the ACS, the highest award in organic chemistry by the ACS, and the 2021 Foresight Institute Feynman Prize for Theory in Nanotechnology. He and his collaborators won the Royal Society of Chemistry 2021 Horizon Prize for the discovery of pericyclases. He was also elected a foreign member of the Chinese Academy of Sciences (CAS) in 2021. He received the ICReDD Award in 2022 and the ICReDD Theoretical Award in 2023, both from Hokkaido University. He shared in a second RSC Horizon Prize with the Garg group for work on strained cumulenes in 2024. He was awarded the 2024 Prix Franco-Américain from the French Chemical Society.

Houk has served on the Advisory Boards of the Chemistry Division of the National Science Foundation, the ACS Petroleum Research Fund, and 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, the Journal of Chemical Theory and Computation, Chemistry – A European Journal, and Topics in Current Chemistry. He was Chair of the Chemistry Section of the AAAS in 2000-2003. He was a Senior Editor of Accounts of Chemical Research from 2005-2015. From 2018-2021, he was the North American Co-Chair of Chemistry – A European Journal. He has been a member of the NIH Medicinal Chemistry and Synthesis and Biological Chemistry Study Sections and the NRC Board of Chemical Sciences and Technology. He was Director of the UCLA Chemistry-Biology Interface Training Program from 2002-2012 and is a member of the UCLA Molecular Biology Institute and the California NanoSystems Institute.

Professor Houk is an authority on theoretical and computational organic chemistry. 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. He collaborates prodigiously with chemists all over the world. Among current interests are the theoretical investigations of mechanisms and design of enzyme-catalyzed reactions, the quantitative modeling of asymmetric reactions used in synthesis, and the dynamics and properties of supramolecular nanomachines, as well as his lifelong interest in the mechanisms and dynamics of pericyclic reactions. He has published about 1600 publications and a physical organic chemistry textbook with Pierre Vogel. He has an h-index of 151.

Research Interests

The Houk Group solves problems in organic and biological chemistry using theoretical and computational methods. Theoretical predictions and designs of new reactions, reagents, and catalysts are tested experimentally by a worldwide network of collaborators. The group is currently heavily involved in the study of dynamics of chemical reactions and the motions and properties of nanomachines.

The Houk Group conducts research in the following areas:

  • Molecular dynamics of chemical reaction mechanisms, especially ambimodal reactions
  • Enzyme mechanisms, selectivities, and design of novel enzymes
  • Pericyclases: enzymes that catalyze pericyclic reactions
  • Mechanisms and design of stereoselective organic reactions and catalysts
  • Pericyclic reaction mechanisms, dynamics, rates, synthetic applications, and biorthogonal chemistry
  • Organometallic reaction mechanisms and CH functionalizations
  • Organic materials, molecular devices, and host-guest chemistry – structures and dynamics

Honors & Awards

  • Herbert Newby McCoy Award, joint with Neil Garg, UCLA, 2025
  • Prix Franco-Américain, French Chemical Society, 2024
  • Organic Chemistry Horizon Prize:  Perkin Prize in Physical Organic Chemistry (Houk/Garg Team), Royal Society of Chemistry, 2024
  • Honorary Fellow, Chinese Chemical Society, 2024
  • Foreign Member, Chinese Academy of Sciences, 2021
  • Feynman Prize for Theory in Advances in Nanotechnology, Foresight Institute, 2021
  • Roger Adams Award in Organic Chemistry, American Chemical Society, 2021
  • Horizon Prize:  Bioorganic Chemistry (Houk/Garg/Tang Team), Royal Society of Chemistry, 2021
  • Honorary Professor, University of Queensland, Brisbane, Australia, 2014
  • Glenn T. Seaborg Medal, UCLA, 2013
  • Society of Postdoctoral Scholars Mentoring Award, UCLA, 2013
  • Fellow, Royal Society of Chemistry, 2012
  • Robert Robinson Award, Royal Society of Chemistry, 2012
  • Member, National Academy of Sciences, 2010
  • Arthur C. Cope Award, American Chemical Society, 2009
  • Fellow, American Chemical Society, 2009
  • Award for Computers in Chemical and Pharmaceutical Research, American Chemical Society, 2003
  • Member, International Academy of Quantum Molecular Science, 2003
  • Fellow, American Academy of Arts and Sciences, 2002
  • Fellow, Japanese Society for the Promotion of Science, 2001
  • Lise Meitner Lecturer, Hebrew University, Jerusalem Israel, 2000
  • Lady Davis Fellow and Visiting Professor, Technion, Israel, 2000
  • Doctor rerum naturalium honoris causa, University of Essen, Germany, 1999
  • Tolman Medal, American Chemical Society Southern California Section, 1999
  • Schrödinger Medal, World Association of Theoretical Organic Chemistry, 1998
  • Herbert Newby McCoy Award, UCLA, 1993
  • Visiting Erskine Fellow, University of Canterbury, Christchurch, New Zealand, 1993
  • James Flack Norris Award in Physical Organic Chemistry, American Chemical Society, 1991
  • Fellow, American Association for the Advancement of Science, 1988
  • Arthur C. Cope Scholar Award, American Chemical Society, 1988
  • Akron Section of the American Chemical Society Award, 1983
  • Von Humboldt U.S. Senior Scientist Award, 1982
  • LSU Distinguished Research Master Award, 1978
  • Alfred P. Sloan Foundation Research Fellowship, 1975-1977
  • Camille and Henry Dreyfus Teacher-Scholar Grant, 1972-1977

Representative Publications

Below is the list of the most recent publications.  For the full list, please visit here.

  • Pengchen Ma, Dennis Svatunek, Zixi Zhu, Dale L. Boger, Xin-Hua Duan, and K. N. Houk: “Computational Studies of Reactions of 1,2,4,5-Tetrazines with Enamines in MeOH and HFIP,” J. Am. Chem. Soc., 146, 18706-18713 (2024). (PDF)

  • Liang-Wen Qi, Torben Rogge, K. N. Houk, and Yixin Lu:  “Iridium Nitrenoid-Enabled Arene C-H Functionalization,” Nature Catal., 7, 934-943 (2024). (PDF)
  • Tianyu Zheng, Jiawei Ma, Haochi Chen, Hao Jiang, Shuo Lu, Zhuangzhi Shi, Fang Liu, K. N. Houk, and Yong Liang:  “Computational Design of Ligands for the Ir-Catalyzed C5-Borylation of Indoles through Tuning Dispersion Interactions,” J. Am. Chem. Soc., 146, 25058-25066 (2024). (PDF)
  • Sara Gutkin, Omri Shelef, Zuzana Babjakova, Laura Anna Tomanova, Matej Babjak, Tal Kopp, Qingyang Zhou, Pengchen Ma, Micha Fridman, Urs Spitz, Kendall N. Houk, and Doron Shabat:  “Boosting Chemiexcitation of Phenoxy-1,2-dioxetanes through 7-Norbornyl and Homocubanyl Spirofusion,” JACS Au, 4, 3558-3566 (2024). (PDF)
  • Sanjoy Adak, Naike Ye, Logan A. Calderone, Meng Duan, Wilson Lubeck, Rebecca J. B. Schaffer, April L. Lukowski, K. N. Houk, Marai-Eirini Pandelia, Catherine L. Drennan, and Bradley S. Moore:  “A Single Diiron Enzyme Catalyzes the Oxidative Rearrangement of Tryptophan to Indole Nitrile,” Nature Chem., 1989-1998 (2024). (PDF)
  • Chen Yang, Kendall N. Houk, Yonatan Dubi, and Xuefeng Guo:  “Reply to:  Questioning Claims of Monitoring the Michael Addition Reaction at the Single-Molecule Level,” Nature Chem., 16, 1770-1771 (2024). (PDF)
  • Christopher R. Travis, Hanne C. Henriksen, Jake R. Wilkinson, Noah K. Schomburg, Joseph W. Treacy, Kelsey M. Kean, K. N. Houk, and Marcey L. Waters:  “WDR5 Binding to Histone Serotonylation Is Driven by and Edge-Face Aromatic Interaction with Unexpected Electrostatic Effects,” J. Am. Chem. Soc., 146, 27451-27459 (2024).  PMCID:  PMC12132056 (PDF)
  • Maya David, Thomas Leirikh, Omri Shelef, Sara Gutkin, Tal Kopp, Qingyang Zhou, Pengchen Ma, Micha Fridman, Kendall N. Houk, and Doron Shabat:  “Chemexcitation Acceleration of 1,2-Dioxetanes by Spiro-Fused Six-Member Rings with Electron-Withdrawing Motifs,” Angew. Chem. Int. Ed., 63, e202410047 (2024). (PDF)
  • Indrajit Paul, Krzysztof A. Konieczny, Roberto Chavez, Jing-Ran Shan, Kendall N. Houk, and Miguel A. Garcia-Garibay:  “Cascade Photoreaction in Crystals:  A Phase Change Caused by a Dewar Benzene Quantum Chain Triggers a Topochemical [2+2] Photodimerization,” J. Am. Chem. Soc., 146, 27988-27922 (2024). (PDF)
  • Grace E. Kunkel, Joseph W. Treacy, Magdalena F. Polite, Hayden R. Montgomery, Evan A. Doud, Kendall N. Houk, Alexander M. Spokoyny, and Heather D. Maynard:  “Heteroelechelic Organometallic PEG Reagents Enable Modular Access to Complex Bioconjugates,” ACS Macro Lett., 13, 1551-1557 (2024). (PDF)
  • Luca McDermott, Zach G. Walters, Sarah A. French, Allison M. Clark, Jiaming Ding, Andrew V. Kelleghan, K. N. Houk, and Neil K. Garg:  “A Solution to the Anti-Bredt Olefin Synthesis Problem,” Science, 386, eadq3519 (2024). (PDF)
  • Martin-Louis Y. Riu, Stasik Popov, Benjamin Wigman, Zhenqi Zhao, Jonathan Wong, Kendall N. Houk, and Hosea Nelson:  “Carbon-Carbon Bond Forming Reactions of Vinyl Cations:  A Personal Perspective,” Eur. J. Org. Chem.,  27, e202400567 (2024). (PDF)
  • Yaling Zhang, Chaoqin Cao, Yuanbin She, Huw M. L. Davies, Yun-Fang Yang, and K. N. Houk:  “Molecular Dynamics of the Davies Ambimodal C-H Functionalization/Cope Rearrangement Reaction,” J. Org. Chem., 89, 17176-17186 (2024). (PDF)
  • Joseph W. Treacy, Elaine Y. Chao, Grace E. Kunkel, Thomas Louis-Goff, James A. R. Tilden, Alexander M. Spokoyny, Heather D. Maynard, and K. N. Houk:  “Electronic Effects of Bidentate P,N-Ligands on the Elementary Steps of Au(I)/Au(III) Reactions Relevant to Cross-Coupling Chemistry,” Org. Lett., 26, 10875-10879 (2024). (PDF)
  • Yilin Guo, Chen Yang, Lei Zhang, Yujie Hu, Jie Hao, Chuancheng Jia, Yang Yang, Yan Xu, Xingxing Li, Fanyang Mo, Yanwei Li, Kendall N. Houk, and Xuefeng Guo:  “Full On-Device Manipulation of Olefin Metathesis for Precise Manufacturing,” Nature Nanotech., 20, 245-254 (2025). (PDF)
  • Chuyu Xiao, Jing-Ran Shan, Wen-Deng Liu, Xingyuan Gao, Jingwei Dai, Zuwei Wang, Wentao Wang, K. N. Houk, and Jiannan Zhao:  “Stereoselective Radical Acylfluoroalkylation of Bicyclobutanes via N-Heterocyclic Carbene Catalysis,” Angew. Chem. Int. Ed., 64, e202416781 (2025). (PDF)
  • Angelos Pistofidis, Pengchen Ma, Zihao Li, Kim Munro, K. N. Houk, and T. Martin Schmeing:  “Structure and Mechanism of Condensation in Non-Ribosomal Peptide Synthesis,” Nature, 638, 270-278 (2025). (PDF)
  • Joseph W. Treacy, James A. R. Tilden, Elaine Y. Chao, Zihuan Fu, Alexander M. Spokoyny, K. N. Houk, and Heather D. Maynard:  “In silico Screening of P,N-Ligands Facilitates Optimization of Au(III)-Mediated S-Arylation,” Chem. Sci., 16, 3878-3887 (2025). (PDF)
  • Martin-Louis Y. Riu, Jing-Ran Shan, K. N. Houk, and Matthew Nava:  “Metal-Ligand Cooperativity Enables Zero-Valent Metal Transfer,” Chem. Sci., 16, 3888-3894 (2025). (PDF)
  • Yuanhang Li, Haiting Ye, Shaohong Wang, Silong Xu, Martin J. Lear, Kendall N. Houk, Pengchen Ma, and Jing Li:  “Light-Dependent Amide or Thioamide Formation of Acylsilanes with Amines Using Elemental Sulfur,” Chem. Eur. J., e202404555 (2025). (PDF)
  • Chen-Yu Chiang, Masao Ohashi, Jessie Le, Pan-Pan Chen, Qingyang Zhou, Songrong Qu, Undramaa Bat-Erdene, Shabnam Hematian, Jose A. Rodriguez, K. N. Houk, Yisong Guo, Joseph A. Loo, and Yi Tang:  “Copper-Dependent Halogenase Catalyses Unactivated C-H Bond Functionalization,” Nature, 638, 126-132 (2025). (PDF)
  • Yilin Guo, Chen Yang, Xinmiao Xie, Yanwei Li, Kendall N. Houk, and Xuefeng Guo:  “Emergent Complexity of Quantum Rotation Tunneling,” Sci. Adv., 11, eads0503 (2025). (PDF)
  • Xin Zhu, Hongliang Chen, Jinying Wang, Agostino Migliore, Xingxing Li, Yanwei Li, Boyu Wang, Chen Yang, Yang Jiao, Jiawen Cao, Caiyao Yang, Chunyan Gao, Suhang He, Kendall N. Houk, Jinlong Yang, J. Fraser Stoddart, Chuancheng Jia, and Xuefeng Guo:  “Single-Electron Catalysis of Reversible Cycloaddtions under Nanoconfinement,” J. Am. Chem. Soc., 147, 6203-6213 (2025). (PDF)
  • Zuodong Sun, Xin Zang, Qingyang Zhou, Masao Ohashi, K. N. Houk, Jiahai Zhou, and Yi Tang:  “Iminium Catalysis in Natural Diels-Alderase,” Nature Catal., 8, 218-228 (2025). (PDF)
  • Christopher J. DeAngelis, Geeta Goyal, Marshall J. Liss, Jessica E. Budwitz, Mary Stuart Herlihy, Audrey V. Conner, Steven E. Wheeler, Pengchen Ma, Miranda Li, K. N. Houk, and Christopher G. Newton:  “Ketenimines as Aza-Dienophiles,” J. Am. Chem. Soc., 147, 6087-6094 (2025). (PDF)
  • Arismel Tena Meza, Christina A. Rivera, Huiling Shao, Andrew V. Kelleghan, K. N. Houk, and Neil K. Garg:  “sigma-Bond Insertion Reactions of Two Strained Diradicaloids,” Nature, 640, 683-690 (2025). (PDF)
  • Hui Liang, Gabriel N Morais, Gang Chen, Wei Tang, Jing Zhao, Chuanyong Wang, K. N. Houk, Shuming Chen, and Jiajia Ma:  “Half-Sandwich Ru(II) Complexes Featuring Metal-Centered Chirality:  Configurational Stabilization by Ligand Design, Preparation via Kinetic Resolution, and Application in Asymmetric Catalysis,” J. Am. Chem. Soc., 147, 6825-6834 (2025). (PDF)
  • Yuqing Chen, Xin Wang, Jing-Ran Shan, Zhixian Wu, Renxu Cao, Yonghong Liu, Yunhe Jin, Erjun Hao, K. N. Houk, and Lei Shi:  “Chemoselective Functionalization of Tertiary C-H Bonds of Allylic Ethers:  Enantioconvergent Access to sec,tert-Vicinal Diols,” Angew. Chem. Int. Ed., 64, e202501924 (2025). (PDF)
  • Marco Galeotti, Andrea Palone, Michela Salamone, Fengjiao Liu, Yanmin Yu, K. N. Houk, and Massimo Bietti:  “Strain Release in Hydrogen Atom Transfer from 1,4-Distributed Cyclohexanes to the Cumyloxy Radical,” Synlett, 36, 1579-1585 (2025). (PDF)
  • Marcus Vinicius Pinto Pereira Junior, Eric P. Geunes, Huiling Shao, Yiran Zhang, Jinkai Cheng, Samantha V. Magpantay, Brandon Q. Mercado, James M. Mayer, Kendall N. Houk, Robert R. Knowles, and Scott J. Miller:  “Enantioselective Hydrodifluoroalkylation of Alkenes with Conformationally Tuned Peptidyl Hydrogen Atom Transfer Catalysts,” J. Am. Chem. Soc., 147, 11412-11424 (2025). (PDF)
  • Qian Yang, Jin-Kai Cheng, Shi-Xiong Tang, Kendall N. Houk, and Fei Wang:  “Stereoselective Synthesis of Tetra- and Tri-Substituted Alkenyl Nitriles via Aminative Ring-Opening of Cyclopropenes with Iron-Aminyl Radical,” Nature Comm., 16, Article 3168 (2025). (PDF)
  • Yilin Guo, Chen Yang, Shuyao Zhao, Kendall N. Houk, and Xuefeng Guo:  “A Robust Single-Molecule Diode with High Rectification Ratio and Integrability,” J. Am. Chem. Soc., 147, 16972-16981 (2025). (PDF)
  • Ching Ching Lam and Kendall N. Houk:  “Exploring Reaction Dynamics Involving Post-Transition State Bifurcations Based on Quantum Mechanical Ambimodal Transition States,” Pure App. Chem., Early Access Article (2025). (PDF)
  • Christopher R. Travis, Jake R. Wilkinson, Ryan G. Dumais, Hanne C. Henriksen, Joseph W. Treacy, Noah K. Schomburg, K. N. Houk, and Marcey L. Waters:  “Negative Cooperativity in the UHRF1 TTD-PHD Dual Domain Masks the Contributions of Cation-pi Interactions Between Trimethyllysine and the TTD Aromatic Cage,” Chem. Eur. J., 31, Article e202500848 (2025).  PMCID:  PMC12188726 (PDF)
  • Dominick C. Witkowski, Daniel W. Turner, Ana S. Bulger, K. N. Houk, and Neil K. Garg:  “Synthesis and Reactivity of Nitrogen-Containing Strained Cyclic 1,2,3-trienes,” Nature Synth., Early Access Article (2025). (PDF)
  • Chen Yang, Shuyao, Yilin Guo, Zexi Hou, Junhao Li, Zhirong Liu, Zitong Liu, Deqing Zhang, Yanwei Li, Kendall N. Houk, and Xuefeng Guo:  “Nano-Second Single-Molecular Reaction Dynamcis for Scalable Synthesis on a Chip,” National Science Rev., Early Access Article (2025). (PDF)