Associate Professor of Chemistry
Organic Chemistry
Office: Reem-Kayden Center 136
845-752-2355
[email protected]
Education
Courses
• Organic Chemistry I: Structure and Mechanism (Chemistry 201)
• Organic Chemistry II: Reactivity and Synthesis (Chemistry 202)
• Advanced Topics in Organic Synthesis (Chemistry 408)
• Laboratory Concepts and Techniques: Synthesis (Chemistry 360)
• Understanding Molecules and Medicine (Chemistry 129)
Research Interests
Our research focuses on the development and study of new organic methods and the application of these methods toward the synthesis of small molecules of biological interest.
Specific Projects
• The design of a general aziridination protocol for dioxenone containing molecules that can be applied toward the synthesis of a diverse array of non-proteinogenic alpha-substituted amino acids.
• Microwave methods development for heterocycle formation, including the anti-microbial pigment violacein and related analogs.
• The applications of a controlled aziridine formation and ring-cleavage in the preparation of complex, biologically active alkaloids and heterocyclic compounds.
• The development of enantioselective photocycloadditions in solution controlled by hydrogen bonding to a chiral host.
Students currently in the McLaughlin Lab:
Alec Waters - class of '19
Alex Bunnell - class of '20
Victoria Wu - class of '20
Brian Lee - class of '20
Waseer Mohammed - class of '20
Recent Bard Graduates (formerly researchers in our lab)
Nusrah Hussain (class of '09) - PhD at Penn; employed at Valspar
Emanuel Krantz (class of '10) - consultant at Farenheit 212
Stavros Velissaris (class of '11) - medical school in Cyprus
Sebastien Cendron (class of '11) - MS at Tufts; employed at Baxalta
Youseung Kim (class of '12) - postbac at NCI; med. student at CCOM
Jing Yang (class of '12) - MS/MBA at University College London/UCLA
Madison Fletcher (class of '12) - PhD, Temple U.; postdoc. UC Irvine
Nicole Camasso (class of '12) - PhD, Michigan; Development Editor JACS
Linda Ibojie (class of '13) - QC chemist at Jos H. Lowenstein & Sons Inc.
Thant Koko (class of '13) - PhD in public health at Wisconsin Med. College
Matthew Norman (class of '14) - analytical chemist at AMRI
E. Berk Atuk (class of '15) - graduate studies at Tulane
Seoyoung Kim (class of '15) - graduate studies at Wisconsin
Anuska Shrestha (class of '15) - PhD candidate at Michigan
Madeline Hwee (class of '16) - research assistant at Rockfeller University
Sabrina Shahid (class of '16) - analytical/QC chemist at Intercos America
Lisa Burke (class of '17) - JET language teacher, Japan
Jeremy Kaplitt (class of '17) - MS in translational medicine, CCNY
Chibuzo (Praise) Anyanwu (class of '18) - graduate studies at Washington
Matthew Lasky (class of '18) - asc. research chemist at MaDermid Enthone
Awards
ACS-PRF Undergraduate Research (UR) Award, "New Methods for Nitrene Generation and Transfer in the Selective Aziridination of Alkenes," awarded 2018-2021.
Research Corporation – Cottrell College Science Award. “Development and synthesis of novel hydrogen-bonding scaffolds and thiourea organocatalysts for enantioselective [2 + 2] photocycloadditions,” awarded 2011-2014.
ACS-PRF Undergraduate New Investigator (UNI) Award, “Aziridination and Retro-Aldol Fragmentation of Dioxenones: Application in the Synthesis of α-Amino Acids and 2-Benzazepine Derivatives,” awarded 2009-2011.
Selected Publications
(undergraduate co-authors are underlined)
Emily C. McLaughlin, Matthew W. Norman, Thant Ko Ko, and Ingrid Stolt. “Three-component synthesis of disubstituted 2H-pyrrol-2-ones: preparation of the violacein scaffold,” Tetrahedron Letters, 2014, 55, 2609-2611.
Jain, S. S.; Sonavane, U. B.; Uppuladinne, M. V. N.; McLaughlin, E. C.; Wang, W.; Black, S.; Joshi, R. R.; “Structural Insights into the Interactions of xpt Riboswitch with Novel Guanine Analogues: A Molecular Dynamics Simulation Study,” Journal of Biomolecular Structure & Dynamics, 2015, 33(2), 234-243.
Emily C. McLaughlin, Anuska Shrestha, Madison H. Fletcher, Nathaniel S. Steinauer, Min-Kyung Shinn, and Sabrina M. Shahid. "A Solvent-free Amidation of Vinylogous Esters via Direct Aziridination," Tetrahedron Letters, 2013, 54, 5461-5463.
Emily C. McLaughlin, David C. Forbes, and Michael P. Doyle, "Guidance for Entering Academics in Organic Chemistry," CUR Quarterly, 2013, 33, (4), 41-48.
Ratnikov, M. O.; Goldmann, P. L.; McLaughlin, E. C.; Doyle, M. P. “Allylic Oxidation Catalyzed by Dirhodium(II)tetrakis[ε-caprolactamate] of tert-Butyldimethylsilyl Protected trans-Dehydroandrosterone.” Organic Syntheses2012, 89, 19-33.
Ratnikov, M. O.; Farkas, L. E.; McLaughlin, E. C.; Chiou. G.; Choi, H.; El Khalafy, S. H.; Doyle, M. P. “Dirhodium Catalyzed Phenol and Aniline Oxidations with T-HYDRO. Substrate Scope and Mechanism of Oxidation” Journal of Organic Chemistry 2011, 76, 2585–2593.
Emily C. McLaughlin, Hojae Choi, Kan Wang, Grace Chiou, and Michael P. Doyle, “Allylic Oxidations Catalyzed by Dirhodium Caprolactamate via Aqueoustert-Butyl Hydroperoxide: The Role of the tert-Butylperoxy Radical,” Journal of Organic Chemistry, 2009, 74, 730-738.
Emily C. McLaughlin and Michael P. Doyle, “Propargylic Oxidation Catalyzed by Dirhodium (II, III) Caprolactamate in Water: Efficient Access to α,β-Acetylenic Ketones,” Journal of Organic Chemistry, 2008, 73, 4317-4319.
Jeffrey D. Winkler and Emily C. McLaughlin, “Intramolecular Photocycloaddition of Dioxenones with Alkynes: Formation of Secondary Photoproducts from Cyclobutene Photoadducts,” Organic Letters, 2005, 7, 227-229.
Jeffrey D. Winkler, Kevin J. Quinn, Colin H. MacKinnon, Steven D. Hiscock, and Emily C. McLaughlin, “A Tandem Diels-Alder Approach to the Synthesis of Eleutherobin.” Organic Letters, 2003, 5, 1805-1808.
Office: Reem-Kayden Center 136
845-752-2355
[email protected]
Education
- Post-doctoral Research Associate, University of Maryland (2008)
Research Advisor: Michael P. Doyle - Ph.D., Organic Chemistry, University of Pennsylvania (2006)
Dissertation Advisor: Jeffrey D. Winkler - B.S., Chemistry, Ohio Northern University (2001)
Courses
• Organic Chemistry I: Structure and Mechanism (Chemistry 201)
• Organic Chemistry II: Reactivity and Synthesis (Chemistry 202)
• Advanced Topics in Organic Synthesis (Chemistry 408)
• Laboratory Concepts and Techniques: Synthesis (Chemistry 360)
• Understanding Molecules and Medicine (Chemistry 129)
Research Interests
Our research focuses on the development and study of new organic methods and the application of these methods toward the synthesis of small molecules of biological interest.
Specific Projects
• The design of a general aziridination protocol for dioxenone containing molecules that can be applied toward the synthesis of a diverse array of non-proteinogenic alpha-substituted amino acids.
• Microwave methods development for heterocycle formation, including the anti-microbial pigment violacein and related analogs.
• The applications of a controlled aziridine formation and ring-cleavage in the preparation of complex, biologically active alkaloids and heterocyclic compounds.
• The development of enantioselective photocycloadditions in solution controlled by hydrogen bonding to a chiral host.
Students currently in the McLaughlin Lab:
Alec Waters - class of '19
Alex Bunnell - class of '20
Victoria Wu - class of '20
Brian Lee - class of '20
Waseer Mohammed - class of '20
Recent Bard Graduates (formerly researchers in our lab)
Nusrah Hussain (class of '09) - PhD at Penn; employed at Valspar
Emanuel Krantz (class of '10) - consultant at Farenheit 212
Stavros Velissaris (class of '11) - medical school in Cyprus
Sebastien Cendron (class of '11) - MS at Tufts; employed at Baxalta
Youseung Kim (class of '12) - postbac at NCI; med. student at CCOM
Jing Yang (class of '12) - MS/MBA at University College London/UCLA
Madison Fletcher (class of '12) - PhD, Temple U.; postdoc. UC Irvine
Nicole Camasso (class of '12) - PhD, Michigan; Development Editor JACS
Linda Ibojie (class of '13) - QC chemist at Jos H. Lowenstein & Sons Inc.
Thant Koko (class of '13) - PhD in public health at Wisconsin Med. College
Matthew Norman (class of '14) - analytical chemist at AMRI
E. Berk Atuk (class of '15) - graduate studies at Tulane
Seoyoung Kim (class of '15) - graduate studies at Wisconsin
Anuska Shrestha (class of '15) - PhD candidate at Michigan
Madeline Hwee (class of '16) - research assistant at Rockfeller University
Sabrina Shahid (class of '16) - analytical/QC chemist at Intercos America
Lisa Burke (class of '17) - JET language teacher, Japan
Jeremy Kaplitt (class of '17) - MS in translational medicine, CCNY
Chibuzo (Praise) Anyanwu (class of '18) - graduate studies at Washington
Matthew Lasky (class of '18) - asc. research chemist at MaDermid Enthone
Awards
ACS-PRF Undergraduate Research (UR) Award, "New Methods for Nitrene Generation and Transfer in the Selective Aziridination of Alkenes," awarded 2018-2021.
Research Corporation – Cottrell College Science Award. “Development and synthesis of novel hydrogen-bonding scaffolds and thiourea organocatalysts for enantioselective [2 + 2] photocycloadditions,” awarded 2011-2014.
ACS-PRF Undergraduate New Investigator (UNI) Award, “Aziridination and Retro-Aldol Fragmentation of Dioxenones: Application in the Synthesis of α-Amino Acids and 2-Benzazepine Derivatives,” awarded 2009-2011.
Selected Publications
(undergraduate co-authors are underlined)
Emily C. McLaughlin, Matthew W. Norman, Thant Ko Ko, and Ingrid Stolt. “Three-component synthesis of disubstituted 2H-pyrrol-2-ones: preparation of the violacein scaffold,” Tetrahedron Letters, 2014, 55, 2609-2611.
Jain, S. S.; Sonavane, U. B.; Uppuladinne, M. V. N.; McLaughlin, E. C.; Wang, W.; Black, S.; Joshi, R. R.; “Structural Insights into the Interactions of xpt Riboswitch with Novel Guanine Analogues: A Molecular Dynamics Simulation Study,” Journal of Biomolecular Structure & Dynamics, 2015, 33(2), 234-243.
Emily C. McLaughlin, Anuska Shrestha, Madison H. Fletcher, Nathaniel S. Steinauer, Min-Kyung Shinn, and Sabrina M. Shahid. "A Solvent-free Amidation of Vinylogous Esters via Direct Aziridination," Tetrahedron Letters, 2013, 54, 5461-5463.
Emily C. McLaughlin, David C. Forbes, and Michael P. Doyle, "Guidance for Entering Academics in Organic Chemistry," CUR Quarterly, 2013, 33, (4), 41-48.
Ratnikov, M. O.; Goldmann, P. L.; McLaughlin, E. C.; Doyle, M. P. “Allylic Oxidation Catalyzed by Dirhodium(II)tetrakis[ε-caprolactamate] of tert-Butyldimethylsilyl Protected trans-Dehydroandrosterone.” Organic Syntheses2012, 89, 19-33.
Ratnikov, M. O.; Farkas, L. E.; McLaughlin, E. C.; Chiou. G.; Choi, H.; El Khalafy, S. H.; Doyle, M. P. “Dirhodium Catalyzed Phenol and Aniline Oxidations with T-HYDRO. Substrate Scope and Mechanism of Oxidation” Journal of Organic Chemistry 2011, 76, 2585–2593.
Emily C. McLaughlin, Hojae Choi, Kan Wang, Grace Chiou, and Michael P. Doyle, “Allylic Oxidations Catalyzed by Dirhodium Caprolactamate via Aqueoustert-Butyl Hydroperoxide: The Role of the tert-Butylperoxy Radical,” Journal of Organic Chemistry, 2009, 74, 730-738.
Emily C. McLaughlin and Michael P. Doyle, “Propargylic Oxidation Catalyzed by Dirhodium (II, III) Caprolactamate in Water: Efficient Access to α,β-Acetylenic Ketones,” Journal of Organic Chemistry, 2008, 73, 4317-4319.
Jeffrey D. Winkler and Emily C. McLaughlin, “Intramolecular Photocycloaddition of Dioxenones with Alkynes: Formation of Secondary Photoproducts from Cyclobutene Photoadducts,” Organic Letters, 2005, 7, 227-229.
Jeffrey D. Winkler, Kevin J. Quinn, Colin H. MacKinnon, Steven D. Hiscock, and Emily C. McLaughlin, “A Tandem Diels-Alder Approach to the Synthesis of Eleutherobin.” Organic Letters, 2003, 5, 1805-1808.