Emily McLaughlin

Emily McLaughlin

Assistant Professor of Chemistry
Director, Chemistry Program
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)
• 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.

• The applications of a controlled aziridine 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:

     Matthew Norman  -  class of '14
     Ingrid Stolt -  class of  '15
     Seoyoung Kim-  class of  '15
     Berk Atuk -  class of  '15
     Anuska Shrestha-  class of  '16
     Sabrina Shahid -  class of ' 16

     Recent Bard Graduates (formerly researchers in our lab)

     Nusrah Hussain (class of '09) - graduate studies at Penn
     Emanuel Krantz (class of '10) - employed at Idea Couture
     Stavros Velissaris (class of '11) - medical school in Cyprus
     Sebastien Cendron (class of '11) - graduate studies at Tufts
     Youseung Kim (class of '12) - postbac fellow at the NCI
     Jing Yang (class of '12) - graduate studies at University College London
     Madison Fletcher (class of '12) - graduate studies at Temple
     Nicole Camasso (class of '12) - graduate studies at Michigan


Awards

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 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)

McLaughlin, E. C.; Shestha, A.; Fletcher, M. H; Steinauer, N. S.; Shinn, M. K.; Shahid, S. M. "A Solvent-free Amidation of Vinylogous Esters via Direct Aziridination," Tetrahedron Letters, 2013, 54, 5461-5463.

McLaughlin, E. C.; Forbes, D. C.; Doyle, M. P. "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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