Publications

27. Stephens, S. M. and Lambert, K. M. “The importance of Atomic Charges for Predicting Site-Selective C-H Borylations” Submitted. 2024.

26. Phadnis, N; Molen, J. A.; Stephens, S. M.; Weierbach, S. M.; Lambert, K. M.; Milligan, J. A. “Green Oxidation of Aromatic Hydrazide Derivatives Using an Oxoammonium Salt” J. Org. Chem. 2024, 89, 8, 5841-5845. [link]

25. Bray, J. M.; Stephens, S. M.; Weierbach, S. M.; Vargas, K.; Lambert, K. M. “Recent advancements in the use of Bobbitt’s salt and 4-acetamido TEMPO” Chem. Commun. 2023, 59, 14063. [link]

24. Stephens, S. M.; Bray, J. M.; Weierbach, S. M.; Adornato, G. M.; Schrider, J. A., Lambert, K. M. “Facile Access to 1,3-Bis(boryl) Dienes to Build Molecular Complexity Through Cycloadditions” Tetrahedron Lett. 2023, 117, 154381. [Link]

23. Lewis, S. G.; Dadum, A. G.; McLean, D.; Buenavista, J.; Myers, J.; Lambert, K. M.; J. Fair “Chemoselective Oxidation of Alcohols in the Presence of Amines Using an Oxoammonium Salt” Tetrahedron 2023, 131, 133226. [Link]

22. Weierbach, S. M.; Reynolds, R. P.; Stephens, S. M.; Vlasakakis, K. V.; Ritter, R. T.; White, O. M.; Patel, N. H.; Hayes, E. C.; Dunmire, S.; Lambert, K. M. “Chemoselective Oxidation of Thiols with Oxoammonium Cations” J. Org. Chem. 2023, 88,11392-11410. [Link]

21. Lambert, K. M.; Kelly, C.; Milligan, J.; Tilley, L.; Reynolds, R. P.; McGuire, K. P.; Anzalone, L.; Del Sesto, K.; Walsh, S. “A practical Oxidation Experiment for Undergraduate Students: Bobbitt’s Salt as a “Green” Alternative” J. Chem. Educ. 2022, 99, 9, 3249–3258. [Link]

20.   Kaetzel, N. D.; Lambert, K. M.*; Kelly, C. B. “Oxidation of Aldehydes to Nitriles with an Oxoammonium Salt: Preparation of Piperonylnitrile” Org. Synth. 2020, 97, 294–313. [Link]

Prior to ODU

19. Jackson, A. C.; Olsen J. T.; Sundstrom, S.; Lambert, K. M.; Wood, J. L. “A Ring Expansion Approach To N-oxy-2,5-diketopiperazines” Tetrahedron Lett. 2022, 99, 153851–153853. [Link]

Graphical abstract: Synthetic studies toward longeracemine: a SmI2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo[2.2.1]heptane framework

18.   Komine, K.; Lambert, K. M.; Savage, Q. R.; Cox, J. B.; Wood, J. L. “Synthetic Studies Toward Longeracemine: A SmI2-mediated Spirocyclization and Rearrangement Cascade to Construct the 2-Azabicyclo[2.2.1]heptane Framework” Chem. Sci. 2020, 11, 9488–9493. [Link]

17.   Lambert, K. M.; Cox, J. B.; Liu, L.; Jackson, A. C.; Wiberg, K. B.; Wood, J. L. “Total Synthesis of (±)‐Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen‐Oxygen Bonds” Angew. Chem. 2020, 59, 9757–9766. [Link]

16.   Lambert, K. M.*; Medley, A. W.; Jackson, A. C.; Markham, L. E.; Wood, J. L. “Synthesis of Chiral Tetramic Acids: Preparation of (S)-5-Benzylpyrrolidine-2,4-dione from L-phenylalanine Methyl Ester Hydrochloride” Org. Synth. 2019, 96, 528-585. [Link]

Image 1

15.   Gayler, K. M.; Lambert, K. M.; Wood, J. L. “Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate” Tetrahedron 2019, 75, 3154–3159. [Link]

14.   Wiberg, K. B.; Bailey, W. F.; Lambert, K. M. “Unrecognized Intramolecular and Intermolecular Attractive Interactions between Fluorine-Containing Motifs and Ether, Carbonyl, and Amino Moieties” J. Org. Chem. 2019, 84, 15463–15469. [Link]

13.   Lambert, K. M.; Eldirany, S. A.; Bobbitt, J. M.; Bailey, W. F. “Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles” Org. Synth. 2018, 95, 60–79. [Link]

Abstract Image

12.   Wiberg, K. B.; Bailey, W. F.; Lambert, K. M.; Stempel, Z. D. “The Anomeric Effect: It’s Complicated” J. Org. Chem. 2018, 83, 5242–5255. [Link]

11.   Lambert, K. M.; Stempel, Z. D.; Wiberg, K. B.; Bailey, W. F. “Experimental Demonstration of a Sizeable Nonclassical CH∙∙∙G Hydrogen Bond in Cyclohexane Derivatives: Stabilization of an Axial Cyano Group” Org. Lett. 2017, 19, 6408–6411. [Link]

Book logo

10.   Bailey, W. F.; Lambert, K. M. “The Importance of Electrostatic Interactions on the Conformational Behavior of Substituted 1,3-Dioxanes: The Case of 5-Phenyl-1,3-dioxane.” In Stereochemistry and Global Connectivity: The Legacy of Ernest L. Eliel Volume 2; Cheng, H. N.; Maryanoff, C. A.; Miller, B. D.; Schmidt, D. G., Eds.;ACS Symposium Series Vol.1258; American Chemical Society: Washington, DC, 2017; Chapter 2,  pp 19–26. [Link]

Abstract Image

9.   Lambert, K. M.*;Stempel, Z. D.; Kiendzior, S. M.; Bartelson, A. L.; Bailey, W. F. “Enhancement of the Oxidizing Power of an Oxoammonium Salt by Modification of a Distal Group” J. Org. Chem. 2017, 82, 11440–11446. [Link]

8.   Bailey, W. F.; Lambert, K. M.; Stempel, Z. D.; Wiberg, K. B.; Mercado, B. Q. “Controlling the Conformational Energy of a Phenyl Group by Tuning the Strength of a Nonclassical CH∙∙∙O Hydrogen Bond: The Case of 5-Phenyl-1,3-dioxane” J. Org. Chem. 2016, 81, 12116–12127. [Link] This article was selected as a Featured Article for J. Org. Chem.

7.   Bartelson, A. L.; Lambert, K. M.; Bobbitt, J. M.; Bailey, W. F. “Recent Developments in the Nitroxide-Catalyzed Oxidation of Amines: Preparation of Imines and Nitriles” Chem. Cat. Chem. 2016, 8, 3421–3430. [Link]

6.   Lambert, K. M.; Bobbitt, J. M.; Eldirany, S. E.; Kissane, L. E.; Sheridan, R. K.; Stempel, Z. D.; Sternberg, F. H.; Bailey, W. F. “Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles.” Chem. Eur. J. 2016, 22, 5156–5159. [Link] This work was featured in Synform 2016, 07, A100–A103. [Link]

5.   Wiberg, K. B.; Lambert, K. M.; Bailey, W. F.; “The Role of CH∙∙∙O Coulombic Interactions in Determining Rotameric Conformations of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans.” J. Org. Chem. 2015, 80, 7884–7889. [Link]

4.   Bailey, W. F.; Lambert, K. M.; Wiberg, K. B.; Mercado, B. Q. “Effect of Remote Aryl Substituents on the Conformational Equilibria of 2,2,-Diaryl-1,3-dioxanes: Importance of Electrostatic Interactions.” J. Org. Chem. 2015, 80, 4108–4115. [Link]

3.   Kelly, C. B.; Lambert, K. M.; Mercadante, M. A.; Ovian, J. M.; Bailey, W. F.; Leadbeater, N. E. “Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt.”  Angew. Chem. Int. Ed. 2015, 54, 4241–4245. [Link] This work was featured inOrg. Process Res. Dev. 2015, 19, 596–610. [Link]

Graphical abstract for this article

2.   Wiberg, K. B.; Lambert, K. M.; Bailey, W. F. “Rotamers of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans: Importance of CH∙∙∙O Coulombic Interactions.” Tetrahedron Lett. 2015, 56, 3438–3440. [Link]

1.   Lambert, K. M.; Bobbitt, J. M.; Eldirany, S. A.; Wiberg, K. B; Bailey, W. F. “Facile Oxidation of Primary  Amines to Nitriles Using an Oxoammonium Salt.” Org. Lett. 2014, 16, 6484–6487. [Link]