Morgan Research Group
Organic Synthesis by Enantioselective Catalysis
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University of North Carolina Wilmington
Aziridine Synthesis and Ring Opening
The cost-effective synthesis of nitrogen-containing small molecules remains an important challenge in organic chemistry. The value of carbon-nitrogen bonds can be highlighted by simply observing their prevalence in commercial pharmaceuticals, where 80-90% of the top 200 medications contain at least one carbon-nitrogen bond. Aziridines, three-membered nitrogen-containing rings, are useful intermediates for the synthesis of small molecules. Our group has become interested in developing new methodologies for the formation and stereoselective ring opening of aziridines. Direct access to enantioenriched tryptamine, phenethylamine, diamine, and amino alcohol derivatives is possible.
Small Molecules for the Treatment of Human Disease
Chiral organic small molecules represent a large class of pharmaceutical active ingredients. Many of our methods projects produce chiral synthons that possess unique structural features. Our group maintains an inventory of compounds that are submitted for enzyme binding assays or whole cell assays to determine if interesting biological activity exists. Specifically, several hundred compounds have been submitted to the Psycoactive Drug Screening Program (PDSP), Lilly's Open Innovation Drug Development (OIDD) program, and the Community for Open Antimicrobial Drug Discovery (CO-ADD).
Independent Career Publications (undergraduate co-authors**)
Quinine-Promoted, Enantioselective Boron-Tethered Diels–Alder Reaction by Anomeric Control of Transition-State Conformation. Katie Scholl, John Dillashaw, Evan Timpy, Yu-hong Lam, Lindsey DeRatt,** Tyler R. Benton,** Jacqueline P. Powell,** K. N. Houk, and Jeremy B. Morgan J. Org. Chem., 2018, 83, 5756-5765. [DOI: 10.1021/acs.joc.8b00938]
Enantiospecific Synthesis of b-Substituted Tryptamines. Heather N. Rubin, Kinney Van Hecke,** Jonathan J. Mills,** Jennifer Cockrell, and Jeremy B. Morgan Org. Lett., 2017, 19, 4976-4979. [DOI: 10.1021/acs.orglett.7b02474]
Palladium-Catalyzed, Enantioselective Heine Reaction. Molly Punk, Charlotte Merkley,** Katlyn Kennedy, and Jeremy B. Morgan ACS Catal. 2016, 6, 4694-4698. [DOI: 10.1021/acscatal.6b01400]
Synthesis of -Substituted Tryptamines by Regioselective Ring Opening of Aziridines. Jesse Kidd,** Kristen Maiden,** and Jeremy B. Morgan Tetrahedron 2016, 72, 3802-3807. [DOI: 10.1016/j.tet.2016.03.031]
Photodegradation of the Antihistamine Cetirizine in Natural Waters. Ralph N. Mead, Seth Barefoot, John R. Helms, Jeremy B. Morgan, and Robert J. Kieber Environ. Toxicol. Chem. 2014, 33, 2240-2245. [DOI: 10.1002/etc.2691]
Scalable Synthesis of N-Acylaziridines from N-Tosylaziridines. Heather Rubin, Jennifer Cockrell, and Jeremy B. Morgan J. Org. Chem. 2013, 78, 8865–8871. [DOI: 10.1021/jo401267j]
Enantioselective Synthesis and Stereoselective Ring Opening of N-Acylaziridines. Jennifer Cockrell, Christopher Wilhelmsen,** Heather Rubin,** Allen Martin, and Jeremy B. Morgan. Angew. Chem., Int. Ed. 2012, 51, 9842-9845. [DOI: 10.1002/anie.201204224]
Investigating the Activity of Quinine Analogues versus Chloroquine Resistant Plasmodium falciparum. Theresa Dinio, Alexander P. Gorka, Andrew McGinniss, Paul D. Roepe, and Jeremy B. Morgan. Bioorg. Med. Chem. 2012, 20, 3292-3297. [DOI: 10.1016/j.bmc.2012.03.042]
Phosphine-Catalyzed Heine Reaction. Allen Martin, Kathleen Casto,** William Morris,** and Jeremy B. Morgan. Org. Lett. 2011, 13, 5444-5447. [DOI: 10.1021/ol202410v]
Iodoetherification of Unactivated Alkenes Catalyzed by Diphosphine Palladium(II) Complexes. Todd A. Doroski,** Matthew R. Cox,** and Jeremy B. Morgan. Tetrahedron Lett. 2009, 50, 5162-5164. [DOI: 10.1016/j.tetlet.2009.06.121]Occurrence of the Artificial Sweetener Sucralose in Coastal and Marine Waters of the United States. Ralph N. Mead, Jeremy B. Morgan, G. Brooks Avery Jr., Robert J. Kieber, Aleksandra M. Kirk, Stephan A. Skrabal, and Joan D. Willey. Marine Chem. 2009, 166, 13-17. [DOI: 10.1016/j.marchem.2009.09.005]
Mentored Publications
Stereocontrolled Synthesis of Functionalized cis-Cyclopentapyrazolidines by 1,3-Dipolar Cycloaddition Reactions of Azomethine Imines. Joshua Gergely, Jeremy B. Morgan, and Larry E. Overman. J. Org. Chem. 2006, 71, 9144-9152. [DOI: 10.1021/jo061537j]
Rh-Catalyzed Enantioselective Diboration of Simple Alkenes: Reaction Development and Substrate Scope. Stephane Trudeau, Jeremy B. Morgan, Mohanish Shrestha, and James P. Morken. J. Org. Chem. 2005, 70, 9538-9544. [DOI: 10.1021/jo051651m]
Catalytic Enantioselective Hydrogenation of Vinyl Bis(boronates). Jeremy B. Morgan and James P. Morken. J. Am. Chem. Soc. 2004, 126, 15338-15339. [DOI: 10.1021/ja044396g]
Catalytic Asymmetric Carbohydroxylation of Alkenes by a Tandem Diboration/Suzuki Cross-Coupling/Oxidation Reaction. Steven P. Miller, Jeremy B. Morgan, Felix J. Nepveux V, and James P. Morken. Org. Lett. 2004, 6, 131-133. [DOI: 10.1021/ol036219a]
Rhodium-Catalyzed Enantioselective Diboration of Simple Alkenes. Jeremy B. Morgan, Steven P. Miller, and James P. Morken. J. Am. Chem. Soc. 2003, 125, 8702-8703. [DOI: 10.1021/ja035851w]
Platinum-Catalyzed Tandem Diboration/Asymmetric Allylboration: Access to Nonracemic Functionalized 1,3-Diols. Jeremy B. Morgan and James P. Morken. Org. Lett. 2003, 5, 2573-2575. [DOI: 10.1021/ol034936z]
Restraint Stress and Corticotropin Releasing Hormone Modulation of Murine Cutaneous POMC mRNA. Melanie S. Flint, Jeremy B. Morgan, Stacey N. Shreve, and Sally S. Tinkle. Stress 2003, 6, 59-62. [DOI: 10.1080/1025389031000088426]