Publications

115. The Backbone Constitution Drives Passive Permeability Independent of Side Chains in Depsipeptide and Peptide Macrocycles
Madelaine P. Thorpe, Abigail N. Smith, Daniel J. Blackwell, Corey R. Hopkins, Bjorn C. Knollmann, Wendell S. Akers, and Jeffrey N. Johnston*
Chem. Sci. 2024, 15, 14977-14987.

 
 

114. Backbone-Determined Antiarrhythmic Structure-Activity Relationships for a Mirror-Image, Oligomeric Depsipeptide Natural Product
Madelaine P. Thorpe, Daniel J. Blackwell, Bjorn C. Knollmann, and Jeffrey N. Johnston*
J. Med. Chem. 2024, 67, 12205

Special issue for Natural Products Driven Medicinal Chemistry

 
 

113. Generality-Driven Catalyst Development: A Universal Catalyst for Enantioselective Nitroalkene Reduction
Zihang Deng, Melanie A. Padalino, Julius E. L. Jan, Sangjun Park, Michael W. Danneman, and Jeffrey N. Johnston*
J. Am. Chem. Soc. 2024, 146, 1269.

Highlighted by Reto Mueller at the Organic Chemistry Portal

 
 


112.
ent-Verticilide B1 inhibits type 2 ryanodine receptor channels and is antiarrhythmic in Casq2-/- mice
Gochman, A.; Do, T. Q.; Kim, K.; Schwarz, J. A.; Thorpe, M. P.; Blackwell, D. J.; Ritschel, P.; Smith, A. N.; Rebbeck, R. T.; Akers, W. S.; Cornea, R. L.; Laver, D. R.; Johnston, J. N.; Knollmann, B. C.*
bioRxiv 2023 & Mol. Pharm. 2024, 105, 194.

 
 

111. RyR2 Binding of an Antiarrhythmic Cyclic Depsipeptide Mapped Using Confocal Fluorescence Lifetime Detection of FRET
Šeflová, J.; Schwarz, J. A.; Smith, A. N.; Svensson, B.; Blackwell, D. J.; Phillips, T. A.; Nikolaienko, R.; Bovo, E.; Rebbeck, R. T.; Zima, A. V.; Thomas, D. D.; Van Petegem, F.; Knollmann, B. C.; Johnston, J. N.*; Robia, S. L.; Cornea, R. L.*
ACS Chem. Biol.
2023, 18, 2290.

 
 

110. The selective RyR2 inhibitor ent-verticilide suppresses atrial fibrillation susceptibility caused by Pitx2 deficiency
Kim, K. ; Blackwell, D.J. ; Yuen, S.L. ; Thorpe, M. P. ; Johnston, J. N. ; Cornea, R.L. ; Knollmann, B. C.*
J. Mol. Cell. Cardiol. 2023, 180, 1.
“Top Original Research Paper of the Year” by the Editors of the J. Mol. Cell. Cardiol. for 2023
Highlighted by Leigh MacMillan in a VUMC Reporter spotlight.

 
 

109. In vivo pharmacokinetic and pharmacodynamic properties of the antiarrhythmic molecule ent-verticilide
Blackwel, D.; Smith, A.; , Do, T. Q.; Gochman, A.; Schmeckpeper, J.; Hopkins, C.; Akers, W.*; Johnston, J. N.*; Knollmann, B.*
J. Pharm. Exptl. Ther. 2023, 385, 205.


 
 


106. Structure-Activity Relationships for the N-Me- versus N-H-Amide Modification to Macrocyclic ent-Verticilide Antiarrhythmics
Smith, A.; Thorpe, M; Blackwell, D; Batiste, S; Hopkins, C; Schley, N; Knollmann, B; Johnston, J. N.
ACS Med. Chem. Lett. 2022, 13, 1755.

Featured in the Virtual Collection - Future of Medicinal Chemistry Collection

Don’t miss the Editorial, including statements from Abby (and Jeff) - Special Collection Editorial

 
 

105. Preparation of N-Aryl Amides by Epimerization-Free Umpolung Amide Synthesis
Crocker, M. S.; Deng, Z. Johnston, J. N.
J. Am. Chem. Soc. 2022, 144.
Featured by Douglass Taber in Org. Chem. Highlights - spectacular reactions

 
 

104. Enantioselective Iodolactonization to Prepare ε-Lactone Rings Using Hypervalent Iodine
Payne, J.; Deng, Z.; Flach, A.; Johnston, J. N.* [†equal contribution]
Chem. Sci. 2022, 13, 7318.

 
 

103. Resolving Bromonitromethane Sourcing by Synthesis: Preparation at the Decagram Scale
Thorpe, M. P.; Smith, A. N.; Crocker, M. S.;Johnston, J. N.
J. Org. Chem. 2022, 87, 5451.

 
 

102. Exercise Causes Arrhythmogenic Remodeling of Intracellular Calcium Dynamics in Plakophilin-2 Deficient Hearts
van Opbergen, C.; Bagwan, N.; Maurya, S; Kim, J.C.; Smith, A; Blackwell, D; Johnston, J.N.; Knollmann, B; Cerrone, M.; Lundby, A; Delmar, M.
Circulation 2022, 145, 1480.
Highlighted in Muscle Cell News

 

101. Fluorine-Induced Diastereodivergence Discovered in an Equally Rare Enantioselective syn-aza-Henry Reaction
Bing, J. A.; Schley, N. D.; Johnston, J. N.
Chem. Sci. 2022, 13, 2614.

 

100. Ring-Size as an Independent Variable in Cyclooligomeric Depsipeptide Antiarrhythmic Activity
Smith, A. N.; Blackwell, D. J.; Knollmann, B. C.; Johnston, J. N.
ACS Med. Chem. Lett. 2021, 12, 1942.

 

99. DFT-Based Stereochemical Rationales for the Bifunctional Brønsted Acid/Base-Catalyzed Diastereodivergent and Enantioselective aza-Henry Reactions of α-Nitro Esters
Struble, T. J.;† Foy, Hayden;† Dudding, T.*; Johnston, J.N. [†equal contribution]
J. Org. Chem. 2021, 86, 15606.

 

98. The Formation of Impossible Rings in Macrocyclooligomerizations for Cyclodepsipeptide Synthesis: The 18-From-12 Paradox
Smith, A. N.; Johnston, J. N..
J. Org. Chem. 2021, 86, 7904.
Related: Batiste, S. M.; Johnston, J. N., Correction to “Evidence for Ion-Templation During Macrocyclooligomerization of Depsipeptides”. J. Am. Chem. Soc. 2021, 143, 6701.
Related: Correction to “Rapid synthesis of cyclic oligomeric depsipeptides with positional, stereochemical, and macrocycle size distribution control”
here.

 

97. RYR2 Channel Inhibition is the Principal Mechanism of Flecainide Action in CPVT
Kryshtal, D. O.; Blackwell, D. J.; Egly, C. L.; Smith, A. N.; Batiste, S. M.; Johnston, J. N.; Laver, D. R.; Knollmann, B. C
Circ. Res. 2021, 128, 321.


96. Substituted Imidazoline Synthesis: A Diastereo- and Enantioselective aza-Henry Route to a Human Proteasome Modulator
Sprague, D. J.; Johnston, J. N.
Org. Lett. 2020, 22, 8496.
Highlighted by P. Kocienski: Synfacts 2021, 17, 17

 

95. Bromonitromethane: Second Update
Vishe, M. N. ; Johnston, J. N.
Encyclopedia of Reagents for Organic Synthesis
2019.


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94. Direct Observation and Analysis of the Halo-Amino-Nitro Alkane Functional Group
Crocker, M. ; Foy, H. ; Tokumaru, K. ; Dudding, T. ; Pink, M. ; Johnston, J. N.
Cell: Chem 2019, 5, 1248-1264
Highlighted by Carol Rouzer in VICB News

 

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93. Unnatural Verticilide Enantiomer Inhibits Type 2 Ryanodine Receptor Mediated Calcium Leak and is Antiarrhythmic
Batiste, S. ; Blackwell, D. ; Kim, K. ; Gomez-Hurtado, N. ; Rebbeck, R. ; Cornea, R. ; Johnston, J. N. ; Knollmann, B.
Proc. Natl. Acad. Sci. 2019, 116, 4810.
Highlighted by Tien Nguyen in Chemical & Engineering News
Highlighted by Carol Rouzer in VICB News
Highlighted by Heidi Hall in Research News Vanderbilt

 
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92. Catalytic, Enantioselective Synthesis of Cyclic Carbamates from Dialkyl Amines by CO2-Capture: Discovery, Development, and Mechanism
Yousefi, R. ; Struble, T. ; Payne, J. L. ; Vishe, M. N. ; Schley, N. D. ; Johnston, J. N.
J. Am. Chem. Soc. 2019, 141, 618.
Highlighted by Carol Rouzer in VICB News

 
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91. Canvass: A Crowd-Sourced, Natural-Product Screening Library for Exploring Biological Space
Kearney, S. E. ; Many ; Other ; Authors ; Johnston, J. N. ; Rohde, J. M.
ACS Cent. Sci. 2019, 4, 1727.

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89. The Inverted Ketene Synthon: A Double Umpolung Approach to Enantioselective β2,3-Amino Amide Synthesis
Vishe, M. N. ; Johnston, J. N.
Chem. Sci. 2019, 10, 1138.
Highlighted by Ben List & Joyce Grimm in Synfacts
Highlighted by Catherine Hodges in ChemistryWorld

 
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88. Continuous Platform To Generate Nitroalkanes On-Demand (in Situ) Using Peracetic Acid-Mediated Oxidation in a PFA Pipes-in-Series Reactor
Tsukanov, S. V. ; Johnson, M. D. ; May, S. A. ; Kolis, S. P. ; Yates, M. H. ; Johnston, J. N.
Org. Process Res. Dev. 2018, 22, 971.

 
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87. Evidence for Ion-Templation During Macrocyclooligomerization of Depsipeptides
Batiste, S. ; Johnston, J. N.
J. Am. Chem. Soc. 2018, 140, 4560.
Highlighted by Carol Rouzer in VICB News

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86. Cluster Preface: Alkene Halofunctionalization
Johnston, J. N. ; Rovis, T.
SynLett 2018, 29, 399.


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85. Biomimetic Desymmetrization of a Carboxylic Acid
Knowe, M. ; Danneman, M. ; Sun, S. ; Pink, M. ; Johnston, J. N.
J. Am. Chem. Soc. 2018, 140, 1998.
Highlighted by Organic Chemistry Highlights: https://www.organic-chemistry.org/Highlights/2018/17December.shtm

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82. MDM2 Antagonists Counteract Drug-Induced DNA Damage
Vilgelm, A. ; Vara, B. ; Johnston, J. N. ; Richmond, A. ; et al.
EBioMedicine 2017, 24, 43.


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81. 1,3,4-Oxadiazole and Heteroaromatic-Fused 1,2,4-Triazole Synthesis using Diverted Umpolung Amide Synthesis
Tokumaru, K. ; Bera, K. ; Johnston, J. N.
Synthesis 2017, 49, 4670.
Thematic Issue on Heterocycle Synthesis, edited by E. Carreira

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79. Rapid Synthesis of Cyclic Oligomeric Depsipeptides with Positional, Stereochemical, and Macrocycle Size-Distribution Control
Batiste, S. ; Johnston, J. N.
Proc. Natl. Acad. Sci. 2016, 113, 14893.
Highlighted by Carol Rouzer in VICB News
Highlighted by David Salisbury in Research News@Vanderbilt
Highlighted by Phys.org

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75. Development of an Intermittent-Flow Enantioselective Aza-Henry Reaction Using an Arylnitromethane and Homogeneous Bronsted Acid−Base Catalyst with Recycle
Tsukanov, S. V. ; Johnston, M. D. ; May, S. A. ; Rosemeyer, M. ; Watkins, M. A. ; Kolis, S. P. ; Yates, M. H. ; Johnston, J. N.
Org. Process Res. Dev. 2016, 20, 215.

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74. A One-Pot Amidation of Primary Nitroalkanes
Schwieter, K. E. ; Johnston, J. N.
Chem. Commun. 2016, 52, 152.

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71. Enantioselective Small Molecule Synthesis by Carbon Dioxide Fixation using a Dual Brønsted Acid Base Organocatalyst
Vara, B. ; Struble, T. ; Wang, W. ; Dobish, M. ; Johnston, J. N.
J. Am. Chem. Soc. 2015, 137, 7302.

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69. Enantioselective Synthesis of D-α-Amino Amides from Aliphatic Aldehydes
Schwieter, K. E. ; Johnston, J. N.
Chem. Sci. 2015, 6, 2590.
Highlighted by Matteo Zanda in Synform 20158, A111
Highlighted by Douglass Taber in Organic Chemistry Portal

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68. Adaptation of a Small Molecule Hydrogen Bond-Donor Catalyst to an Enantioselective Hetero-Diels-Alder Reaction Hypothesized for Brevianamide Biosynthesis
Sprague, D. ; Nugent, B. M. ; Yoder, R. A. ; Vara, B. ; Johnston, J. N.
Org. Lett. 2015, 17, 880.
ACS Editor's Choice - Open Access

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67. Mdm3 and Aurora Kinase A Inhibitors Synergize to Block Melanoma Growth by Driving Apoptosis and Immune Clearance of Tumor Cells
Vilgelm, A. E. ; Liu, Y. ; Hawkins, O. E. ; Davis, T. ; Smith, J. ; Weller, K. P. ; Horton, L. W. ; McClain, C. M. ; Ayers, G. D. ; Turner, D. C. ; Essaka, D. C. ; Stewart, C. F. ; Sosman, J. A. ; Kelley, M. C. ; Ecsedy, J. A. ; Johnston, J. N. ; Richmond, A.
Cancer Res 2015, 75, 181.

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65. Umpolung Amide Synthesis Using Substoichiometric NIS and Oxygen as a Terminal Oxidant
Schwieter, K. E. ; Shen, B. ; Shackleford, J. ; Leighty, M. ; Johnston, J. N.
Org. Lett. 2014, 16, 4714.

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64. Organocatalytic, Diastereo- and Enantioselective Synthesis of Nonsymmetric cis-Stilbene Diamines: A Platform for the Preparation of Single Enantiomer cis-Imidazolines for Protein-Protein Inhibition
Vara, B. ; Mayasundari, A. ; Tellis, J. ; Danneman, M. ; Arredondo, V. ; Davis, T. ; Min, J. ; Finch, K. ; Guy, R. K. ; Johnston, J. N.
J. Org. Chem. 2014, 79, 6913.

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61. Preparation of (−)-Nutlin-3 Using Enantioselective Organocatalysis at Decagram Scale
Davis, T. ; Vilgelm, A. E. ; Richmond, A. ; Johnston, J. N.
J. Org. Chem. 2013, 78, 10605.
Highlighted by 'Synthesis of (-)-Nutlin-3' Kocienski, P. Synfacts 201410, 1 [doi: 10.1055/s-0033-1340328]

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60. Serratezomine A
Pigza, J. A. ; Johnston, J. N.
2012, 0, 131.


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59. Total Synthesis of the Lycopodium Alkaloid Serratezomine A Using Free Radical-Mediated Vinyl Amination to Prepare a β-Stannyl Enamine Linchpin
Pigza, J. A. ; Han, J. ; Chandra, A. ; Mutnick, D. ; Pink, M. ; Johnston, J. N.
J. Org. Chem. 2013, 78, 822.
Selected as JOC Featured Article by Editors

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58. VNI cures the acute and chronic experimental Chagas disease
Villalta, F. ; Dobish, M. ; Nde, P. N. ; Kleshchenko, Y. Y. ; Hargrove, T. Y. ; Johnson, C. A. ; Waterman, M. R. ; Johnston, J. N. ; Lepesheva, G. I.
J. Infect. Dis. 2013, 208, 504.

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57. Organocatalytic, Enantioselective Synthesis of VNI: A Robust Therapeutic Development Platform for Chagas, a Neglected Tropical Disease
Dobish, M. ; Villalta, F. ; Waterman, M. R. ; Lepesheva, G. I. ; Johnston, J. N.
Org. Lett. 2012, 14, 6322.
Highlighted by 'Synthesis of (+)-VNI' Kocienski, P. Synfacts 20139, 250 [doi: 10.1055/s-0032-1318124]

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56. Enantioselective Synthesis of α-Oxy Amides via Umpolung Amide Synthesis
Leighty, M. ; Shen, B. ; Johnston, J. N.
J. Am. Chem. Soc. 2012, 134, 15233.
Highlighted by 'Synthesis of LY411575' Kocienski, P. Synfacts 20128, 1293 [doi: 10.1055/s-0032-1317560]

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54. Achiral Counterion Control of Enantioselectivity in a Brønsted Acid Catalyzed Iodolactonization
Dobish, M. ; Johnston, J. N.
J. Am. Chem. Soc. 2012, 134, 6068.
Highlighted by List, Monaco 'Achiral Counteranion Effects in an Asymmetric Iodolactonization' Synfacts20128, 673.

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53. Preparation of a Chiral Bis(Amidine) Ligand: Pyrrolidine Bis(Amidine)
Davis, T. ; Dobish, M. ; Schwieter, K. E. ; Chun, A. C. ; Johnston, J. N.
Org. Synth. 2012, 89, 380.

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51. Total Synthesis of the Chlorine-Containing Hapalindoles K, A, G
Chandra, A. ; Johnston, J. N.
Angew. Chem. Int. Ed. 2011, 50, 7641.

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50. Enantioselective Organocatalysis in the Synthesis of Stilbene cis-Diamines: A Concise Preparation of (–)-Nutlin-3, a Potent p53/MDM2 Inhibitor
Davis, T. ; Johnston, J. N.
Chem. Sci. 2011, 2, 1076.
Highlighted by Simon Hadlington in Chemistry World 2011 March 25.
Highlighted by Borman, S. 'Chiral Route To Key Anticancer Agent' Chemical & Engineering News, April 11, 201189, 41.
Highlighted by 'Synthetic Protocol Published for Promising Anticancer Compound' Future Medicinal Chemistry 20113, 779.

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47. Geometric Restraint Drives On- and Off-Pathway Catalysis by the Escherichia Coli Menaquinol:Fumarate Reductase
Tomasiak, T.M. ; Archuleta, T.L. ; Andrell, J. ; Luna-Chavez, C. ; Davis, T. ; Sarwar, M. ; Ham, A.J. ; McDonald, H. ; Yankovskaya, V. ; Stern, H.A. ; Johnston, J. N. ; Maklashina, E. ; Cecchini, G. ; Iverson, T.M.
J. Biol. Chem. 2011, 286, 3047.

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45. Transformations of Alkenes: Aziridination
Muchalski, H. ; Johnston, J. N.
Science of Synthesis 2011, 1, 155.


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42. Preparation of Isopropyl 2-Diazoacetyl(phenyl)carbamate
Muchalski, H. ; Doody, A. ; Troyer, T. ; Johnston, J. N.
Org. Synth. 2011, 88, 212.

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41. Umpolung Reactivity in Amide and Peptide Synthesis
Shen, B. ; Makley, D. ; Johnston, J. N.
Nature 2010, 464, 1027.
Highlighted by Jaenicke, L. in Chemie in unserer Zeit 201044, 319
Highlighted in Organic Process Research & Development 2010, 14, 1052-1060 (doi: 10.1021/op100229b)
Highlighted in Chemical & Engineering News, June 28, 2010 Borman, S. 'New Route to Amide Formation'
Highlighted by Scheidt, K. 'Organic chemistry: Amide bonds made in reverse' Nature 2010465 , 1020 (doi:10.1038/4651020a)
Highlighted in Pharmaceutical Technology August 2010, Van Arnum, P. 'Exploring Chiral Chemistry'
Highlighted in Pharmaceutical Technology May 2011, Van Arnum, P. 'A Marriage of Small Molecules and Biologics'

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38. A Brønsted Acid Catalyzed syn-Selective Glycolate Mannich Reaction
Troyer, T. ; Muchalski, H. ; Johnston, J. N.
Chem. Commun. 2009, 41, 6195.

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36. Total Synthesis of the Lycopodium Alkaloid (+)-Serratezomine A
Chandra, A. ; Pigza, J. A. ; Han, J. ; Mutnick, D. ; Johnston, J. N.
J. Am. Chem. Soc. 2009, 131, 3470.
Highlighted in Kocienski, P.; Schmidt, A. W. SynFacts 2009, 9, 946

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34. A Diastereo- and Enantioselective Synthesis of α-Substituted anti-α,α-Diaminophosphonic Acid Derivatives
Wilt, J. C. ; Pink, M. ; Johnston, J. N.
Chem. Commun. 2008, 35, 4177.
selected as ‘Hot Article’ by Chemical Communications reviewers and editor

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33. A Preparation of Enantiomerically Enriched Axially Chiral β-Diketimines: Synthesis of (-)- and (+)-IAN Amine
Cortright, S. B. ; Counceller, C. ; Wilt, J. C. ; Perkins, B. ; Johnston, J. N.
Org. Lett. 2008, 10, 2445.

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32. A Diastereo- and Enantioselective Synthesis of α-Substituted syn-α,β-Diamino Acids
Singh, A. ; Johnston, J. N.
J. Am. Chem. Soc. 2008, 130, 5866.
Highlighted in List, B.; Muller, S. SynFacts 2008, 7, 757

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31. Free Radical-Mediated Aryl Amination: Convergent Two- and Three-Component Couplings to Chiral 2,3-Disubstituted Indolines
Viswanathan, R. ; Smith, C. R. ; Prabhakaran, E. ; Johnston, J. N.
J. Org. Chem. 2008, 73, 3040.

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29. Synthesis of the ABC- and D-Ring Systems of the Indole Alkaloid Ambiguine G
Chandra, A. ; Viswanathan, R. ; Johnston, J. N.
Org. Lett. 2007, 9, 5027.

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27. Synthesis of an Advanced Intermediate En Route to Mitomycin C
Williams, A. L. ; Srinivasan, J. ; Johnston, J. N.
Org. Lett. 2006, 8, 6047.

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25. Chiral Proton Catalysis: pKa Determination for a BAM-HX Brønsted Acid
Hess, A. ; Yoder, R. A. ; Johnston, J. N.
SynLett 2006, 1, 147.



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23. Brønsted Acid-Promoted Olefin Aziridination and Formal anti-Aminohydroxylation
Mahoney, J. M. ; Smith, C. R. ; Johnston, J. N.
J. Am. Chem. Soc. 2005, 127, 1354.

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22. Free Radical-Mediated Aryl Amination: A Practical Synthesis of (R)- and (S)-7-Azaindoline-α-Amino Acid
Srinivasan, J. ; Burks, H. E. ; Smith, C. R. ; Viswanathan, R. ; Johnston, J. N.
Synthesis 2005, 2, 330.


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20. IAN-Amines: Chiral C2-Symmetric Zirconium(IV) Complexes from Readily Modified Axially Chiral C1-Symmetric β-Diketimines
Cortright, S. B. ; Huffman, J. C. ; Yoder, R. A. ; Coalter III, J. N. ; Johnston, J. N.
Organometallics 2004, 23, 2238.

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19. Chiral Proton Catalysis: A Catalytic Enantioselective Direct Aza-Henry Reaction
Nugent, B. M. ; Yoder, R. A. ; Johnston, J. N.
J. Am. Chem. Soc. 2004, 126, 3418.
Highlighted in Science Concentrates, Chemical & Engineering News, March 22, 2004

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16. Free Radical-Mediated Vinyl Amination: A Mild, General Pyrrolidinyl Enamine Synthesis

Nugent, B. M. ; Williams, A. L. ; Prabhakaran, E. ; Johnston, J. N.

Tetrahedron 2003, 59, 8877.

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15. The First Azacyclopentenyl Carbinyl Radical Isomerizations (ACCRI): Independent Use of Steric and Electronic (Polarization) Effects as Gating Elements
Viswanathan, R. ; Mutnick, D. ; Johnston, J. N.
J. Am. Chem. Soc. 2003, 125, 7266.
Highlighted in Science & Technology Concentrates, Chemical & Engineering News, June 9, 2003

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13. Free Radical-Mediated Vinyl Amination: Access to N,N-Dialkyl Enamines and their β-Stannyl and β-Thio Derivatives
Prabhakaran, E. ; Williams, A. L. ; Nugent, B. M. ; Nailor, K. E. ; Johnston, J. N.
Org. Lett. 2002, 4, 4197.

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