Scott E Denmark

Search results

• 2023

  Albert Eschenmoser (1925-2023)

  Denmark, S. E. & Sorensen, E. J., Sep 15 2023, In: Science (New York, N.Y.). 381, 6663, p. 1158 1 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  • Biological Products 100%

• A machine-learning tool to predict substrate-adaptive conditions for Pd-catalyzed C–N couplings

  Rinehart, N. I., Saunthwal, R. K., Wellauer, J., Zahrt, A. F., Schlemper, L., Shved, A. S., Bigler, R., Fantasia, S. & Denmark, S. E., Sep 1 2023, In: Science. 381, 6661, p. 965-972 8 p.

  Research output: Contribution to journal › Article › peer-review

  • Palladium 100%
  • Machine Learning 74%
  • Carbon 64%
  • Nitrogen 64%
  • Computer Neural Networks 42%

• Extrapolative Prediction Of Enantioselectivity Enabled By Computer-driven Workflow, New Molecular Representations And Machine Learning

  Denmark, S. E., Zahrt, A. F., Henle, J. J., Rose, B. T., Wang, Y. & Darrow, W., May 30 2023, U.S. Patent No. 11664093

  Research output: Patent
• 2022

  Application of Machine Learning and Reaction Optimization for the Iterative Improvement of Enantioselectivity of Cinchona-Derived Phase Transfer Catalysts

  Lexa, K. W., Belyk, K. M., Henle, J., Xiang, B., Sheridan, R. P., Denmark, S. E., Ruck, R. T. & Sherer, E. C., Mar 18 2022, In: Organic Process Research and Development. 26, 3, p. 670-682 13 p.

  Research output: Contribution to journal › Review article › peer-review

  • machine learning 100%
  • catalysts 72%
  • optimization 51%
  • Catalyst 32%
  • Application 24%

• Enantioselective Inter- and Intramolecular Sulfenofunctionalization of Unactivated Cyclic and (Z)-Alkenes

  Matviitsuk, A., Panger, J. L. & Denmark, S. E., 2022, In: ACS Catalysis. 12, p. 7377-7385 9 p.

  Research output: Contribution to journal › Article › peer-review

  • Olefins 100%
  • Nucleophiles 87%
  • Enantioselectivity 84%
  • Ions 38%
  • Catalysts 35%

• Extraction Of Selected Platinum-group Metals From Supported Catalyst

  Denmark, S. E. & Ibrahim, M. Y. S., Aug 30 2022, U.S. Patent No. 11427887

  Research output: Patent

• High-Level Data Fusion Enables the Chemoinformatically Guided Discovery of Chiral Disulfonimide Catalysts for Atropselective Iodination of 2-Amino-6-arylpyridines

  Rose, B. T., Timmerman, J. C., Bawel, S. A., Chin, S., Zhang, H. & Denmark, S. E., Dec 21 2022, In: Journal of the American Chemical Society. 144, 50, p. 22950-22964 15 p.

  Research output: Contribution to journal › Article › peer-review

  • Halogenation 100%
  • Data fusion 79%
  • Catalysts 63%
  • alpha-aminopyridine 48%
  • Pyridines 45%

• Potassium Trimethylsilanolate-Promoted, Anhydrous Suzuki-Miyaura Cross-Coupling Reaction Proceeds via the "boronate Mechanism": Evidence for the Alternative Fork in the Trail

  Delaney, C. P., Marron, D. P., Shved, A. S., Zare, R. N., Waymouth, R. M. & Denmark, S. E., Mar 16 2022, In: Journal of the American Chemical Society. 144, 10, p. 4345-4364 20 p.

  Research output: Contribution to journal › Article › peer-review

  • potassium trimethylsilanolate 100%
  • Palladium 59%
  • Boronate 49%
  • palladium 48%
  • Potassium 47%
• 2021

  A Conformer-Dependent, Quantitative Quadrant Model

  Zahrt, A. F., Rinehart, N. I. & Denmark, S. E., May 7 2021, In: European Journal of Organic Chemistry. 2021, 17, p. 2343-2354 12 p.

  Research output: Contribution to journal › Article › peer-review

  • quadrants 100%
  • catalysts 76%
  • capture effect 43%
  • imines 39%
  • rhodium 35%

• A Unified Strategy for the Asymmetric Synthesis of Highly Substituted 1,2-Amino Alcohols Leading to Highly Substituted Bisoxazoline Ligands

  Shrestha, B., Rose, B. T., Olen, C. L., Roth, A., Kwong, A. C., Wang, Y. & Denmark, S. E., Feb 19 2021, In: Journal of Organic Chemistry. 86, 4, p. 3490-3534 45 p.

  Research output: Contribution to journal › Article › peer-review

  • Alcohol 60%
  • Electrophile 49%
  • Imine 44%
  • Ligand 43%
  • Reaction Yield 40%

• Catalytic, Enantioselective Diamination of Alkenes

  Tao, Z. L. & Denmark, S. E., Nov 3 2021, In: Synthesis (Germany). 53, 21, p. 3951-3962 12 p., ss-2021-r0324-sr.

  Research output: Contribution to journal › Review article › peer-review

  • Cycloaddition 100%
  • Olefins 88%
  • Electrons 74%
  • Oxidation-Reduction 64%
  • Alkene 52%

• Catalytic, Enantioselective Syn-Oxyamination of Alkenes

  Mumford, E. M., Hemric, B. N. & Denmark, S. E., Aug 25 2021, In: Journal of the American Chemical Society. 143, 33, p. 13408-13417 10 p.

  Research output: Contribution to journal › Article › peer-review

  • Amino alcohols 100%
  • Amino Alcohols 91%
  • Alkenes 78%
  • Olefins 60%
  • Oxazoline 59%

• Computational methods for training set selection and error assessment applied to catalyst design: Guidelines for deciding which reactions to run first and which to run next

  Zahrt, A. F., Rose, B. T., Darrow, W. T., Henle, J. J. & Denmark, S. E., Apr 2021, In: Reaction Chemistry and Engineering. 6, 4, p. 694-708 15 p.

  Research output: Contribution to journal › Article › peer-review

  • Computational methods 100%
  • Catalysts 80%
  • Error 71%
  • Set theory 60%
  • Homogeneous Catalysis 39%

• Dreams, False Starts, Dead Ends, and Redemption: A Chronicle of the Evolution of a Chemoinformatic Workflow for the Optimization of Enantioselective Catalysts

  Rinehart, N. I., Zahrt, A. F., Henle, J. J. & Denmark, S. E., May 4 2021, In: Accounts of chemical research. 54, 9, p. 2041-2054 14 p.

  Research output: Contribution to journal › Article › peer-review

  • Catalyst 100%
  • Error 11%

• Heteroaryl-Heteroaryl, Suzuki-Miyaura, Anhydrous Cross-Coupling Reactions Enabled by Trimethyl Borate

  Kassel, V. M., Hanneman, C. M., Delaney, C. P. & Denmark, S. E., Sep 1 2021, In: Journal of the American Chemical Society. 143, 34, p. 13845-13853 9 p.

  Research output: Contribution to journal › Article › peer-review

  • Trimethyl Borate 100%
  • Borates 85%
  • potassium trimethylsilanolate 76%
  • borate 75%
  • Bromides 74%

• Leveraging Machine Learning for Enantioselective Catalysis: From Dream to Reality

  Rinehart, N. I., Zahrt, A. F. & Denmark, S. E., Aug 2021, In: Chimia. 75, 7-8, p. 592-597 6 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  • Catalyst 98%

• Lewis Base Catalyzed, Sulfenium Ion Initiated Enantioselective, Spiroketalization Cascade

  Hilby, K. M. & Denmark, S. E., Nov 5 2021, In: Journal of Organic Chemistry. 86, 21, p. 14250-14289 40 p.

  Research output: Contribution to journal › Article › peer-review

  • Alkene 37%
  • Ion 27%
  • Reaction Yield 14%
  • Cyclization Reaction 13%
  • Alcohol 10%

• Stereochemical language in supramolecular polymer chemistry: How we can do better

  Palmans, A. R. A., Meijer, E. W. & Denmark, S. E., Jun 15 2021, In: Journal of Polymer Science. 59, 12, p. 1171-1174 4 p.

  Research output: Contribution to journal › Article › peer-review

  • polymer chemistry 100%
  • Supramolecular Polymer 74%
  • Asymmetry 62%
  • Chirality 60%
  • asymmetry 45%

• Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation

  Menard, T., Laverny, A. & Denmark, S. E., Nov 5 2021, In: Journal of Organic Chemistry. 86, 21, p. 14290-14310 21 p.

  Research output: Contribution to journal › Article › peer-review

  • Alkene 64%
  • Occurrence in Nature 37%
  • Pharmaceutical 33%
  • Phenol 32%
  • Reaction Yield 18%
• 2020

  Anhydrous, homogeneous, suzuki-miyaura cross-coupling of boronic esters using potassium trimethylsilanolate

  Delaney, C. P., Heyboer, E. M. & Denmark, S. E., 2020, In: Organic Syntheses. 97, p. 245-261 17 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

• Asymmetric Hydrogenation of Unfunctionalized Tetrasubstituted Acyclic Olefins

  Bigler, R., Mack, K. A., Shen, J., Tosatti, P., Han, C., Bachmann, S., Zhang, H., Scalone, M., Pfaltz, A., Denmark, S. E., Hildbrand, S. & Gosselin, F., Feb 10 2020, In: Angewandte Chemie - International Edition. 59, 7, p. 2844-2849 6 p.

  Research output: Contribution to journal › Article › peer-review

  • Acyclic Olefin 100%
  • Hydrogenation 76%
  • Olefins 72%
  • Enantioselectivity 30%
  • Alkene 21%

• Catalytic, Enantioselective Sulfenofunctionalization of Alkenes: Development and Recent Advances

  Matviitsuk, A., Panger, J. L. & Denmark, S. E., Nov 2 2020, In: Angewandte Chemie - International Edition. 59, 45, p. 19796-19819 24 p.

  Research output: Contribution to journal › Review article › peer-review

  • Olefins 100%
  • Ions 76%
  • Nucleophiles 69%
  • Alkene 59%
  • Ion 33%

• Cautionary Guidelines for Machine Learning Studies with Combinatorial Datasets

  Zahrt, A. F., Henle, J. J. & Denmark, S. E., Nov 9 2020, In: ACS Combinatorial Science. 22, 11, p. 586-591 6 p.

  Research output: Contribution to journal › Article › peer-review

  • Chemical Entity 100%
  • Chemistry 45%
  • Amount 33%
  • Catalyst 32%

• Demystifying the asymmetry-amplifying, autocatalytic behaviour of the Soai reaction through structural, mechanistic and computational studies

  Athavale, S. V., Simon, A., Houk, K. N. & Denmark, S. E., Apr 1 2020, In: Nature Chemistry. 12, 4, p. 412-423 12 p.

  Research output: Contribution to journal › Article › peer-review

  • Pyridine 83%
  • Pyridine-3-Carbaldehyde 70%
  • Substrates 53%
  • Spectroscopic analysis 40%
  • Density functional theory 38%

• Development of a Computer-Guided Workflow for Catalyst Optimization. Descriptor Validation, Subset Selection, and Training Set Analysis

  Henle, J. J., Zahrt, A. F., Rose, B. T., Darrow, W. T., Wang, Y. & Denmark, S. E., Jul 1 2020, In: Journal of the American Chemical Society. 142, 26, p. 11578-11592 15 p.

  Research output: Contribution to journal › Article › peer-review

  • Workflow 100%
  • Catalysts 76%
  • Set theory 57%
  • Conformations 38%
  • Empiricism 37%

• Enantioselective Synthesis of γ-Lactams by Lewis Base Catalyzed Sulfenoamidation of Alkenes

  Panger, J. L. & Denmark, S. E., Apr 3 2020, In: Organic Letters. 22, 7, p. 2501-2505 5 p.

  Research output: Contribution to journal › Article › peer-review

  • Lewis Bases 100%
  • Lewis base 85%
  • Alkenes 77%
  • Lactams 70%
  • alkenes 63%

• Potassium trimethylsilanolate enables rapid, homogeneous suzuki-miyaura cross-coupling of boronic esters

  Delaney, C. P., Kassel, V. M. & Denmark, S. E., Jan 3 2020, In: ACS Catalysis. 10, 1, p. 73-80 8 p.

  Research output: Contribution to journal › Article › peer-review

  • Potassium 100%
  • Quantitative Yield 87%

• Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future

  Zahrt, A. F., Athavale, S. V. & Denmark, S. E., Feb 12 2020, In: Chemical reviews. 120, 3, p. 1620-1689 70 p.

  Research output: Contribution to journal › Review article › peer-review

  • Chirality 100%
  • Application 33%
  • Chemistry 31%
  • Catalyst 22%

• Structural contributions to autocatalysis and asymmetric amplification in the soai reaction

  Athavale, S. V., Simon, A., Houk, K. N. & Denmark, S. E., Oct 28 2020, In: Journal of the American Chemical Society. 142, 43, p. 18387-18406 20 p.

  Research output: Contribution to journal › Article › peer-review

  • pyridine 99%
  • pyrimidine 94%
  • amplification 73%
  • Pyrimidine 68%
  • Organic Chemistry 67%
• 2019

  (R)-n,n’-dimethyl-1,1’-binaphthyldiamine

  Denmark, S. E. & Ryabchuk, P. G., 2019, In: Organic Syntheses. 96, p. 382-399 18 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

• A Dinuclear Mechanism Implicated in Controlled Carbene Polymerization

  Zhukhovitskiy, A. V., Kobylianskii, I. J., Thomas, A. A., Evans, A. M., Delaney, C. P., Flanders, N. C., Denmark, S. E., DIchtel, W. R. & Toste, F. D., Apr 24 2019, In: Journal of the American Chemical Society. 141, 16, p. 6473-6478 6 p.

  Research output: Contribution to journal › Article › peer-review

  • carbene 100%
  • Polymerization 58%
  • Living polymerization 51%
  • Carbene 50%
  • Palladium 34%

• Catalytic, Enantioselective syn-Diamination of Alkenes

  Tao, Z., Gilbert, B. B. & Denmark, S. E., Dec 4 2019, In: Journal of the American Chemical Society. 141, 48, p. 19161-19170 10 p.

  Research output: Contribution to journal › Article › peer-review

  • Alkenes 100%
  • Olefins 76%
  • Alkene 45%
  • Nucleophiles 33%
  • Enantioselectivity 32%

• Dynamically Chiral Helical Polymers: A New Frontier in Asymmetric Catalysis?

  Denmark, S. E., Jul 24 2019, In: ACS Central Science. 5, 7, p. 1117-1119 3 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  • Catalysis 100%
  • Catalysts 63%
  • Polymers 54%
  • Solvent 35%

• Enantio- and Diastereoselective, Lewis Base Catalyzed, Cascade Sulfenoacetalization of Alkenyl Aldehydes

  Matviitsuk, A. & Denmark, S. E., Sep 2 2019, In: Angewandte Chemie - International Edition. 58, 36, p. 12486-12490 5 p.

  Research output: Contribution to journal › Article › peer-review

  • Acetal 68%
  • Ions 63%
  • Aldehyde 47%
  • One Pot Reaction 30%
  • Solvent 16%

• Enantioselective, lewis base-catalyzed, intermolecular sulfenoamination of alkenes

  Roth, A. & Denmark, S. E., Sep 4 2019, In: Journal of the American Chemical Society. 141, 35, p. 13767-13771 5 p.

  Research output: Contribution to journal › Article › peer-review

  • Lewis Bases 100%
  • Alkenes 77%
  • Olefins 59%
  • Sulfur 58%
  • Benzylamine 57%

• Evaluating continuous chirality measure as a 3D descriptor in chemoinformatics applied to asymmetric catalysis

  Zahrt, A. F. & Denmark, S. E., Mar 29 2019, In: Tetrahedron. 75, 13, p. 1841-1851 11 p.

  Research output: Contribution to journal › Article › peer-review

  • Cheminformatics 100%
  • Catalysis 73%
  • Forests 73%
  • Chirality 57%
  • Catalyst 8%

• Lewis base activation of silicon lewis acids

  Rossi, S. & Denmark, S. E., Dec 10 2019, Organosilicon Chemistry: Novel Approaches and Reactions. Wiley, p. 333-415 83 p.

  Research output: Chapter in Book/Report/Conference proceeding › Chapter

  • Lewis Acid 80%
  • Catalyst 12%

• Organoselenium-catalyzed enantioselective syn-dichlorination of unbiased alkenes

  Gilbert, B. B., Eey, S. T. C., Ryabchuk, P., Garry, O. & Denmark, S. E., Aug 2 2019, In: Tetrahedron. 75, 31, p. 4086-4098 13 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

  • Alkenes 100%
  • Alkene 45%
  • Synthetic Chemistry Techniques 26%
  • Diselenide 19%
  • Chlorides 17%

• Prediction of higher-selectivity catalysts by computer-driven workflow and machine learning

  Zahrt, A. F., Henle, J. J., Rose, B. T., Wang, Y., Darrow, W. T. & Denmark, S. E., Jan 18 2019, In: Science. 363, 6424, eaau5631.

  Research output: Contribution to journal › Article › peer-review

  • Cheminformatics 100%
  • Machine Learning 69%
  • Workflow 67%
  • Empiricism 51%
  • Support Vector Machine 37%

• Preface for volume 100

  Denmark, S. E., 2019, In: Organic Reactions. 100, p. xxi-xxvii

  Research output: Contribution to journal › Editorial › peer-review

• Preface to volume 97

  Denmark, S. E., 2019, In: Organic Reactions. 97, p. vii-ix

  Research output: Contribution to journal › Editorial › peer-review

• Preface to volume 98

  Denmark, S. E., 2019, In: Organic Reactions. 98, p. vii-x

  Research output: Contribution to journal › Editorial › peer-review

• Preface to volume 99

  Denmark, S. E., 2019, In: Organic Reactions. 99, p. vii-ix

  Research output: Contribution to journal › Editorial › peer-review

• Preparation of a diisopropylselenophosphoramide catalyst and its use in enantioselective sulfenoetherification

  Denmark, S. E., Ryabchuk, P., Chi, H. M. & Matviitsuk, A., 2019, In: Organic Syntheses. 96, p. 400-417 18 p.

  Research output: Contribution to journal › Article › peer-review

  Open Access

• Unusual Kinetic Profiles for Lewis Base-Catalyzed Sulfenocyclization of ortho -Geranylphenols in Hexafluoroisopropyl Alcohol

  Robb, K. A., Athavale, S. V. & Denmark, S. E., 2019, In: Synlett. 30, 14, p. 1656-1661 6 p.

  Research output: Contribution to journal › Article › peer-review

  • Polyene 100%
  • Alcohol 52%
  • Solvent Effect 41%
  • Electronic Property 35%
• 2018

  Catalytic Nucleophilic Allylation Driven by the Water-Gas Shift Reaction

  Denmark, S. E., Matesich, Z. D., Nguyen, S. T. & Milicevic Sephton, S., Jan 5 2018, In: Journal of Organic Chemistry. 83, 1, p. 23-48 26 p.

  Research output: Contribution to journal › Article › peer-review

  • Aldehyde Allylation 100%
  • Aliphatic Aldehyde 79%
  • Allylation 78%
  • Oxirane 77%
  • Benzaldehyde 64%

• Elucidating the Role of the Boronic Esters in the Suzuki-Miyaura Reaction: Structural, Kinetic, and Computational Investigations

  Thomas, A. A., Zahrt, A. F., Delaney, C. P. & Denmark, S. E., Mar 28 2018, In: Journal of the American Chemical Society. 140, 12, p. 4401-4416 16 p.

  Research output: Contribution to journal › Article › peer-review

  • Palladium 100%
  • Boron 94%
  • palladium 82%
  • Esters 66%
  • ester 65%

• Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1,2-Boronate Migration

  Tao, Z., Robb, K. A., Panger, J. L. & Denmark, S. E., Nov 21 2018, In: Journal of the American Chemical Society. 140, 46, p. 15621-15625 5 p.

  Research output: Contribution to journal › Article › peer-review

  • Lewis Bases 100%
  • Esters 50%
  • ester 50%
  • Enantioselectivity 33%
  • Aryl Group 18%

• Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes

  Tao, Z., Robb, K. A., Zhao, K. & Denmark, S. E., Mar 14 2018, In: Journal of the American Chemical Society. 140, 10, p. 3569-3573 5 p.

  Research output: Contribution to journal › Article › peer-review

  • Lewis Bases 100%
  • Polyenes 98%
  • Polyene 57%
  • hinokiol 56%
  • ferruginol 51%

• Investigating the Enantiodetermining Step of a Chiral Lewis Base Catalyzed Bromocycloetherification of Privileged Alkenes

  Böse, D. & Denmark, S. E., Mar 1 2018, In: Synlett. 29, 4, p. 433-439 7 p., st-2017-b0700-c.

  Research output: Contribution to journal › Article › peer-review

  • Alkene 64%
  • Catalyst 37%