Emily McLaughlin

Emily McLaughlin

Associate Dean of the College
Associate Professor of Chemistry

Organic Chemistry

Office: Reem-Kayden Center 136
Phone: 845-752-2355
E-mail: mclaughl@bard.edu


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 Letters2014, 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 ShresthaMadison H. FletcherNathaniel S. SteinauerMin-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 Syntheses 2012, 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.


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