Assistant Professor
Chemistry & Biochemistry

Kyle Lambert

757-683-3650
The Lambert Research Group

CHEMISTRY BUILDING 4501 ELKHORN AVE
NORFOLK, 23529

Kyle was born and raised in Columbia, Connecticut. He attended the University of New Haven where he developed an interest in organic chemistry while pursing undergraduate research under the direction of Prof. Pier Cirillo, exploring ways to construct alkaloid natural products. In addition to chemistry, while at UNH, he competed as a pole vaulter on the varsity track and field team. Kyle graduated with two Bachelor of Science degrees in chemistry and forensic science in 2012. In the fall of 2012, Kyle enrolled in graduate studies at the University of Connecticut and joined Prof. Bill Bailey’s group. His doctoral work focused the development of selective oxidations using oxoammonium salts and investigations into the role of electrostatic interactions in the conformational equilibria of saturated heterocycles. During his free time in graduate school, Kyle was an assistant high school track and field coach and had the opportunity to coach a number of talented athletes at the conference, state, New England, and national levels. Kyle obtained his Ph.D. in chemistry in 2017. Following his graduate studies he left his home state of Connecticut and moved to Waco, Texas in order to pursue postdoctoral studies in Prof. John Wood’s laboratory at Baylor University. While in the Wood lab, Kyle conducted research in the area of natural product total synthesis and developed a ring-expansion strategy to access diketopiperazines and alkaloids that contain synthetically labile nitrogen-oxygen bonds. Kyle was able to obtain a NIH Ruth L. Kirschstein NRSA Postdoctoral Fellowship in 2018 in order to further develop this chemistry. Kyle moved to Virginia to began his independent career as an Assistant Professor of Chemistry within the Department of Chemistry and Biochemistry at Old Dominion University in the summer of 2020. When Kyle is not in the lab, he enjoys fishing, boating, and being outdoors hiking or running.

Contracts, Grants and Sponsored Research

Lambert , K. M . "New Synthetic Methods to Access Natural Products Possessing Unique and Challenging Architectures of Biological Relevance" $4,000. Old Dominion University. January 1, 2022 - May 15, 2022
Lambert, K. "Metal-Free and Environmentally Benign Oxidants for Disulfide Bond Formation" $10,000. Old Dominion University. May 15, 2021 - May 14, 2022

Expertise

Chemistry
Organic Chemistry-Synthetic Method Development, Natural Product Total Synthesis, Organocatalysis, Reaction Mechanisms

Research Interests

Synthetic Methods, Natural Product Synthesis, Reaction Mechanisms, Computational Chemistry; Dr. Lambert's research interests are in the development of novel synthetic methods and the total synthesis of biologically relevant natural products. Our interest lies in the development of robust methodologies, particularly those involving transition metal and nitroxide catalysts, to access the complex architectures found within natural products, as well as, core structural motifs that are of interest to both medicinal and synthetic chemists. We have an additional interest in gaining a fundamental understanding of the mechanistic underpinnings of our developed chemistry, and often employ both experimental and computational methods to do so.

Articles

Komine, K., Lambert, K., Savage, Q. R., Cox, J. B. and Wood, J. L. (2020). Synthetic studies toward longeracemine: a SmI 2-mediated spirocyclization and rearrangement cascade to construct the 2-azabicyclo [2.2. 1] heptane framework. Chemical Science.
Lambert, K., Cox, J. B.., Liu, L., Jackson, A. C.., Yruegas, S., Wiberg, K. B.. and Wood, J. L.. (2020). Total Synthesis of (+/-)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 59 (24) , pp. 9757-9766.
Lambert, K., Medley, A. W.., Jackson, A. C.., Markham, L. E.. and Wood, J. L.. (2019). Synthesis of Chiral Tetramic Acids: Preparation of (S)-5Benzylpyrrolidine-2,4-dione from L-Phenylalanine Methyl Ester Hydrochloride. ORGANIC SYNTHESES 96 , pp. 528-+.
Gayler, K. M.., Lambert, K. and Wood, J. L.. (2019). Synthetic studies towards the penicisulfuranols: Synthesis of an advanced spirocyclic diketopiperazine intermediate. TETRAHEDRON 75 (24) , pp. 3154-3159.
Wiberg, K. B.., Bailey, W. F.. and Lambert, K. (2019). Unrecognized Intramolecular and Intermolecular Attractive Interactions between Fluorine-Containing Motifs and Ether, Carbonyl, and Amino Moieties. JOURNAL OF ORGANIC CHEMISTRY 84 (9) , pp. 5783-5789.
Lambert, K., Eldirany, S. A.., Bobbitt, J. M.. and Bailey, W. F.. (2018). Catalytic, Metal-Free Oxidation of Primary Amines to Nitriles. ORGANIC SYNTHESES 95 , pp. 60-+.
Wiberg, K. B.., Bailey, W. F.., Lambert, K. and Stempel, Z. D.. (2018). The Anomeric Effect: It's Complicated. JOURNAL OF ORGANIC CHEMISTRY 83 (9) , pp. 5242-5255.
Lambert, K., Stempel, Z. D.., Kiendzior, S. M.., Bartelson, A. L.. and Bailey, W. F.. (2017). Enhancement of the Oxidizing Power of an Oxoammonium Salt by Electronic Modification of a Distal Group. JOURNAL OF ORGANIC CHEMISTRY 82 (21) , pp. 11440-11446.
Lambert, K., Stempel, Z. D.., Wiberg, K. B.. and Bailey, W. F.. (2017). Experimental Demonstration of a Sizeable Nonclassical CH···G Hydrogen Bond in Cyclohexane Derivatives: Stabilization of an Axial Cyano Group. ORGANIC LETTERS 19 (23) , pp. 6408-6411.
Bailey, W. F.., Lambert, K., Stempel, Z. D.., Wiberg, K. B.. and Mercado, B. Q.. (2016). 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. JOURNAL OF ORGANIC CHEMISTRY 81 (24) , pp. 12116-12127.
Lambert, K., Bobbitt, J. M.., Eldirany, S. A.., Kissane, L. E.., Sheridan, R. K.., Stempel, Z. D.., Sternberg, F. H.. and Bailey, W. F.. (2016). Metal-Free Oxidation of Primary Amines to Nitriles through Coupled Catalytic Cycles. CHEMISTRY-A EUROPEAN JOURNAL 22 (15) , pp. 5156-5159.
Bartelson, A. L.., Lambert, K., Bobbitt, J. M.. and Bailey, W. F.. (2016). Recent Developments in the Nitroxide-Catalyzed Oxidation of Amines: Preparation of Imines and Nitriles. CHEMCATCHEM 8 (22) , pp. 3421-3430.
Kelly, C. B.., Lambert, K., Mercadante, M. A.., Ovian, J. M.., Bailey, W. F.. and Leadbeater, N. E.. (2015). Access to Nitriles from Aldehydes Mediated by an Oxoammonium Salt. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 54 (14) , pp. 4241-4245.
Bailey, W. F.., Lambert, K., Wiberg, K. B.. and Mercado, B. Q.. (2015). Effect of Remote Aryl Substituents on the Conformational Equilibria of 2,2-Diaryl-1,3-dioxanes: Importance of Electrostatic Interactions. JOURNAL OF ORGANIC CHEMISTRY 80 (8) , pp. 4108-4115.
Wiberg, K. B., Lambert, K. and Bailey, W. F. (2015). Rotamers of phenyl substituted 1, 3-dioxanes and tetrahydropyrans: importance of CH⋯ O Coulombic interactions. Tetrahedron Letters 56 (23) , pp. 3438--3440.
Wiberg, K. B.., Lambert, K. and Bailey, W. F.. (2015). The Role of CH···O Coulombic Interactions in Determining Rotameric Conformations of Phenyl Substituted 1,3-Dioxanes and Tetrahydropyrans. JOURNAL OF ORGANIC CHEMISTRY 80 (16) , pp. 7884-7889.
Lambert, K., Bobbitt, J. M.., Eldirany, S. A.., Wiberg, K. B.. and Bailey, W. F.. (2014). Facile Oxidation of Primary Amines to Nitriles Using an Oxoammonium Salt. ORGANIC LETTERS 16 (24) , pp. 6484-6487.

Book Chapters

Bailey, W. F. and Lambert, K. (2017). The Importance of Electrostatic Interactions on the Conformational Behavior of Substituted 1, 3-Dioxanes: The Case of 5-Phenyl-1, 3-dioxane Stereochemistry and Global Connectivity: The Legacy of Ernest L. Eliel Volume 2 (pp. 19--26) American Chemical Society.

Presentations

Lambert, K. M., Jackson, A. C. and Wood, J. L. (June 23, 2019). “Accessing N-Hydroxydiketopiperazine Natural Products” Poster 46th National Organic Chemistry Symposium Indiana University, Bloomington, IN.
Lambert, K. M., Cox, J. B., Jackson, A. C. and Wood, J. L. (June 17, 2019). “The Total Synthesis of (±)-Phyllantidine and Efforts Towards Natural Products Containing a N–O Bond” Poster 2019 Heterocyclic Compounds GRC Salve Regina University, Newport, RI.
Cox, J. B., Liu, L., Lambert, K. M. and Wood, J. L. (May 24, 2019). “A Ring Expansion Strategy Toward the Securinega Alkaloids” Poster 2019 TexSyn IV Conference Waco, Texas.
Lambert, K. M., Jackson, A. C., Medley, A. W., Markham, L. E. and Wood, J. L.. (May 24, 2019). “Accessing N-Hydroxydiketopiperazine Natural Products” Poster 2019 TexSyn IV Conference Waco, TX.
Gayler, K. M., Lambert, K. M. and Wood, J. L. (May 24, 2019). “Synthetic Studies Towards the Penicisulfuranols: Synthesis of an Advanced Spirocyclic Diketopiperazine intermediate.” Poster 2019 TexSyn IV Conference Waco, TX.
Lambert, K. M. and Wood, J. L. (July 16, 2018). “Accessing N-Hydroxydiketopiperazine Natural Products” Poster 2018 Organic Reactions and Processes GRC Stonehill College, Easton, MA.
Lambert, K. M., Bailey, W. F., Stempel, Z. D., Wiberg, K. B. and Mercado, B. Q. (April , 2017). “Tuning the conformational equilibria in saturated heterocycles through the manipulation of a non-classical CH---O hydrogen bond: The importance of electrostatic interactions within small molecules” Poster 253rd National Meeting of the American Chemical Society San Francisco, CA, .
Ovian, J., Kelly, C. B., Hamlin, T., Loman, J., Mercadante, M. A., Bailey, W. F., Tilley, L. J. and Leadbeater, N. E. (August , 2016). “Oxoammonium salts: Powerful yet practical reagents for oxidation and oxidative functionalization in chemistry” Poster 252nd National Meeting of the American Chemical Society Philadelphia, PA.
Lambert, K. M. (February 19, 2016). “Conformational Studies of Saturated Heterocycles: The Importance of Electrostatic Interactions” Lecture West Haven, CT.
Lambert, K. M., Eldirany, S. A. and Bailey, W. F. (August , 2015). “Access to Nitriles Mediated by Bobbitt’s Salt, an Environmentally Benign and Recyclable Oxidant” Oral Presentation 250th National Meeting of the American Chemical Society Boston, MA.
Eldirany, S. A., Lambert, K. M., Bailey, W. F., Leadbeater, N. E., Bobbitt, J. M., Wiberg, K. B., Kelly, C. B., Mercadante, M. A. and Ovian, J. M. (April 6, 2015). “Bobbitt’s Salt as a Mild Oxidant to Access the Nitrile Functionality” Poster 38th R.T. Major Symposium Storrs, CT,.
Lambert, K. M. and Bailey, W. F. (April 6, 2015). “Conformational Control by Remote Substituents in 2,2-Diaryl-1,3-dioxanes: The Importance of Electrostatic Interactions” Poster 38th R.T. Major Symposium Storrs, CT.
Lambert, K. M. (February 20, 2015). “4-Acetamido-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate as a Mild Oxidant to Access the Nitrile Functionality” Lecture West Haven. CT.
Lambert, K. M., Bailey, W. F. and Wiberg, K. B. (August , 2014). “Conformational Control by Remote Substituents in 2,2-Diaryl-1,3-dioxanes: The Importance of Electrostatic Interactions” Poster 248th National Meeting of the American Chemical Society San Francisco, CA.
  • 2018: National Institutes of Health Ruth Kirschstein Postdoctoral Fellowship , National Institutes of Health
  • 2017: ACS Division of Organic Chemistry Travel Award, ACS Division of Organic Chemistry
  • 2017: Connecticut Chemistry Research Award, University of Connecitcut
  • 2016: UCONN Doctoral Fellowship, University of Connecticut
  • 2014: William L. Masterton Award for Outstanding Teaching, University of Connecticut
  • 2013: Thomas Chu Fellowship, University of Connecticut
  • 2012: Faculty Distinguished Scholar-Athlete, University of New Haven
  • 2012: Henry C. Lee Forensic Science Award, University of New Haven
  • 2012: Outstanding Teaching Assistant in Chemistry, University of New Haven
  • 2012: Walter B. Jewell Award , University of New Haven
  • 2011: Faculty Distinguished Student Athlete, University of New Haven

Organizational Chart