For a better experience, click the Compatibility Mode icon above to turn off Compatibility Mode, which is only for viewing older websites.

Fraser Fleming, PhD

Fraser Fleming, PhD

Professor of Chemistry
Department of Chemistry
Office: Disque Hall 306
Phone: 215.895.2644

Additional Sites: Fleming Group


  • Oregon State University, Post-doctoral fellow, 1990-1992
  • University of British Columbia (Canada) Ph.D. Organic Chemistry, 1990
  • Massey University (New Zealand), B.S. (Hons.) Chemistry, 1986

Curriculum Vitae:

Download [PDF]

Research Interests:

  • Rapidly constructing biologically relevant scaffolds as potential pharmaceutical leads
  • Metalated nitriles as potent nucleophiles for hindered bond construction
  • Metalated isocyanides as precursors to peptide mimics


Fraser Fleming earned his BS (Hons.) at Massey University, New Zealand, in 1986 and a PhD under the direction of Edward Piers at the University of British Columbia, Canada, in 1990. After postdoctoral research with James D. White at Oregon State University he joined the faculty at Duquesne University, Pittsburgh, in 1992. In 2013 he took a temporary position as a program director at the National Science Foundation working in the Synthesis Program and the Catalysis Program. His research interests lie in stereochemistry and organometallics, particularly as applied to the reactions of nitriles and isonitriles.

Selected Publications:

  • "Electrophile-Dependent Alkylations of Lithiated γ-Alkoxyalkenenitriles" Pitta, B. R.; Steward, O. W.; Fleming, F. F. J. Org. Chem. 2018, 83, 2753-2762.
  • "Electrophile-Directed Diastereoselective Oxonitrile Alkylations" Chepyshev, S. V. Pitta, B. R.; Vangala, S. R.; Lujan-Montelongo, J. A.; Steward, O. W.; Fleming, F. F. Chem. Eur. J. 2018, 24, 2850-2853.
  • "Sulfone–Metal Exchange–Alkylation of Sulfonylnitriles" Yang, X.; Nath, D.; Gau, M. R.; Steward, O. W.; Fleming, F. F. Angew. Chem., Int. Ed. 2017, 56, 7257-7260.
  • "Alkenyl Isocyanide Conjugate Additions: A Rapid Route to γ-Carbolines" Chepyshev, S. V.; Montelongo, J. A. L.; Chao, A; Fleming, F. F. Angew. Chem., Int. Ed. 2017, 56, 4310-4313. Pub Med #28295938 NIHMS915234.
  • "Direct Conversion of Nitriles to Alkene 'Isonitriles'" Li, Y.; Fleming, F. F. Angew. Chem., Int. Ed. 2016, 55, 14770-14773.
  • "Oxoalkene Isonitriles: Addition-Cyclization Cascade to Oxazoles" Chao, A.; Lujan-Montelongo, J. A.; Fleming, F. F. Org. Lett. 2016, 18, 3062-3065.
  • "Cyclic Alkenenitriles: Copper-Catalyzed Deconjugative γ-Alkylation" Yang, X.; Nath, D.; Morse, J.; Ogle, C.; Yurtoglu, E.; Altundas, R. Fleming, F. F. J. Org. Chem. 2016, 81, 4098−4102.
  • "Isonitrile Alkylations: A Rapid Route to Imidazo[1,5-a]pyridines" Li, Y.; Chao, A.; Fleming, F. F. Chem. Commun. 2016, 52, 2111-2113. PMC4729585.
  • "Enantioselective Installation of Quaternary Centers in Cyclic Oxonitriles" Gunes, Y.; Arcelik, N.; Sahin, E.; Fleming, F. F.; Altundas, R. Eur. J. Org. Chem. 2015, 81, in press.
  • "Chemoselective Alkylations with N- and C-Metalated Nitriles" Yang, X.; Nath, D.; Fleming, F. F. Org. Lett. 2015, pending revision.
  • "Metalated Nitriles: SNi' Cyclizations with a Propargylic Electrophile" Lu, P.; Pakkala, V. S.; Evanseck, J.; Fleming, F. F. Tetrahedron Lett. 2015, 56,3216-3219.
  • "Alkyl Sulfinates: Formal Nucleophiles for Synthesizing TosMIC Analogs" Montelongo, J. A. L.; Estevez, A. O.; Fleming, F. F. Eur. J. Org. Chem. 2015, 1602-1605.
  • "Arylthio-Metal Exchange of α-Arylthioalkanenitriles" Nath, D.; Skilbeck, M.; Coldham, I.; Fleming, F. F. Org. Lett. 2014, 16, 62−65.
  • "Dithiolopyranthione Synthesis, Spectroscopy, and an Unusual Reactivity with DDQ" Pimkov, I. V.; Nigam, A.; Venna, K.; Fleming, F. F.; Solntsev, P. V.; Nemykin, V. N.; Basu, P. J. Heterocyclic Chem. 2013, 50, 879-886.
  • "Metalated Nitriles: SNi and SNi' Installation of Contiguous Quaternary-Tertiary and Quaternary-Quaternary Centers" Lujan-Montelongo, J. A.; Lu, P.; Liu, W.; Fleming, F. F. Chem. Eur. J. 2013, 19, 8746-8750.
  • "Metalated Nitriles: N- and C-Coordination Preferences of Li, Mg, and Cu Cations" Purzycki, M.; Liu, W.; Hilmersson, G.; Fleming, F. F. Chem. Commun. 2013, 49, 4700-4702.
  • "Preparation of 3-Oxocyclohex-1ene-1-carbonitrile" Lujan-Montelongo, J. A.; Fleming, F. F.; Hughes, D. Org. Synth. 2013, 90, 229-239.
  • "Sulfinylnitriles: Sulfinyl-Metal Exchange-Alkylation Strategies" Nath, D.; Fleming, F. F. Chem. Eur. J. 2013, 19, 2023-2029.
  • "g- and d-Hydroxynitriles: Diastereoselective Electrophile-Dependent Alkylations" Mycka, R. J.; Eckenhoff, W. T.; Steward, O. W.; Barefoot, N. Z.; Fleming, F. F. Tetrahedron, 2013, 69,366-376.