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272 Brown Laboratories
University of Delaware
Department of Chemistry and Biochemistry
Newark, DE 19716302-831-0191
Born: 10/09/1971 in Philadelphia, PA
1993-1998 Columbia University, New York, NY 10027
Degrees Awarded: Ph.D., 1998; M.Phil, 1997; M.A., 1994
Advisor: Prof. Thomas J. Katz
Dissertation Title: Synthesis of Conjugated Helical Polymers, Cyclophanes, Metal Complexes and Phthalocyanines
1989-1993 Princeton University, Princeton, NJ, 08544
A. B., Chemistry, Magna Cum Laude
Advisor: Prof. Maitland Jones, Jr.
Thesis Title: The Phenylcarbene Rearrangement as a Source of Real Carbenes
as of July 2011, Professor, University of Delaware, Department of Chemistry and Biochemistry, Newark, DE 19716
July 2007-present, Associate Professor, University of Delaware, Department of Chemistry and Biochemistry, Newark, DE 19716
July 2001-2007, Assistant Professor, University of Delaware, Department of Chemistry and Biochemistry, Newark, DE 19716
August 1998-May 2001, NIH Postdoctoral Fellow, Massachusetts Institute of Technology, Cambridge, MA 02139, Laboratories of Professor Stephen L. Buchwald
2007 Thieme Journal Award: from the editorial board of Synthesis and Synlett
2006 NSF CAREER Award2005 Eli Lilly Lecturer, Northwestern University
2005 Plenary Lecturer at statewide organic symposium, University of Missouri
1999-01 National Institute of Health Postdoctoral Fellow, MIT
1998 Pegram Award: For excellence in graduate research, Columbia University
1996 Columbia Chemistry Department Award: For the advancement of undergraduate laboratory research
1995 Julian M. Miller Award for Excellence in Teaching, Columbia University
1995-97 Kanagawa Academy of Science and Technology Research Fellow, Columbia University
1993 Magna Cum Laude, Princeton University
1992 Pfizer Undergraduate Summer Fellowship in Synthetic Organic Chemistry, Princeton University
50) Taylor, M. T.; Blackman, M. L.; Dmitrenko, O.; Fox, J. M. “Design and Synthesis of Highly Reactive Dienophiles for the Tetrazine-trans-Cyclooctene Ligation” J. Am. Chem. Soc. 2011, ASAP.
49) Selvaraj, R.; Liu, S.; Hassink, M.; Huang, C.-w.; Yap, L.-p.; Park, R.; Fox, J. M.; Li, Z.; Conti, P. S. “Tetrazine-trans-cyclooctene ligation for the rapid construction of integrin αvβ3 targeted PET tracer based on a cyclic RGD peptide” Bioorganic and Medicinal Chemistry Letters 2011, ASAP.
48) Hassink, M.; Liu, X.; Fox, J. M. “Copper-catalyzed Synthesis of Allenoates from a-Substituted a-Diazoesters” Org. Lett. 2011, ASAP. PMCID in process; NIHMSID: NIHMS288587.
47) DeAngelis, A.; Shurtleff, V. W.; Dmitrenko, O.; Fox, J. M. J. Am. Chem. Soc. 2011, 133, 1650. PMCID in process; NIHMSID # 268105.
46) Dong, Z.; Bai, S.; Yap, G. P. A.; Fox, J. M. “Interplay between Diamine Structure and Absolute Helicity in Ni-salen Metallofoldamers” Chem. Commun. 2011, 47, 3781-3783.
45) Li, Z.; Cai, H.; Hassink, M.; Blackman, M. L.; Brown, R. C. D.; Conti, P. S.; Fox, J. M. "Tetrazine-trans-Cyclooctene Ligation for the Rapid Construction of F-18 Labeled Probes” 2010, 46, 8043-8045.
44) Dong, Z.; Plampin, J. N. III; Yap, G. P. A.; Fox, J. M. ‘Minimalist Endgroups for Control of Absolute Helicity in Salen- and Salophen-based Metallofoldamers’ Org. Lett. 2010, 12, 4002–4005.
43) DeAngelis, A.; Boruta, D. T.; Lubin, J.-B.; Plampin, J. N. III, Fox, J. M. “The Chiral Crown Conformation in Paddlewheel Complexes” Chemical Communications 2010, 4541-4543.
42) Xie, X.; Yang, Z.; Fox, J. M. “Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift" J. Org. Chem. 2010, 75, 3847–3850.
41) Fisher, L. A.; Zhang, F.; Yap, G. P. A.; Fox, J. M. “Weak absolute helicity direction in Ni–salen by trans-cyclohexane-(1R,2R)-diamine” Inorg. Chim. Acta. 2010, 364, 259-260.
40) DeAngelis, A.; Dmitrenko, O.; Yap, G. P. A.; Fox, J. M. “Chiral Crown Conformation of Rh2(S-PTTL)4: Enantioselective Cyclopropanation with α-Alkyl-α-diazoesters” J. Am. Chem. Soc. 2009, 131, 7230–7231.
39) Tarwade, V.; Liu, X.; Yan, N.; Fox, J. M. “Directed Carbozincation Reactions of Cyclopropene Derivatives” J. Am. Chem. Soc. 2009, 131, 5382-5383.
38) DeAngelis A.; Taylor M. T.; Fox, J. M. “Unusually Reactive and Selective Carbonyl Ylides for Three-component Cycloaddition Reactions” J. Am. Chem. Soc. 2009, 131, 1101-1105.
37) Blackman, M. L.; Royzen, M.; Fox, J. M. "The Tetrazine Ligation: Fast Bioconjugation Based on Inverse-electron-demand Diels-Alder Reactivity" J. Am. Chem. Soc. 2008, 130, 13518–13519.
36) Fisher, L. A.; Fox, J. M. "Studies on the Stability of Cycloprop-2-ene Carboxylate Dianions and Reactions with Electrophiles" J. Org. Chem. 2008, 73, 8474–8478.
35) Tarwade, V.; Dmitrenko, O.; Bach, R. D.; Fox, J. M. "The Curtius Rearrangement of Cyclopropyl- and Cyclopropenoyl Azides. A Combined Theoretical and Experimental Mechanistic Study” J. Org. Chem. 2008, 73, 8189–8197.
34) Pallerla, M. K.; Yap, G. P. A.; Fox, J. M. “Co-complexes Derived from Alkene Insertion to Alkyne-dicobaltpentacarbonyl Complexes: Insight into the Regioselectivity of Pauson-Khand Reactions of Cyclopropenes” J. Org. Chem. 2008 73, 6137–6141.
33) Panne, P.; DeAngelis, A.; Fox, J. M. “Rh-Catalyzed Intermolecular Cyclopropanation with α-Alkyl-α-diazoesters: Catalyst-Dependent Chemo- and Diastereoselectivity” Org Lett. 2008, ASAP.
32) Yan, N.; Liu, X.; Pallerla, M.; Fox, J. M. “ Synthesis of Stable Derivatives of Cycloprop-2-ene Carboxylic Acid” J. Org. Chem. 2008, 73, 4283-4286.
31) Royzen, M.; Yap, G. P. A.; Fox, J. M. “A Photochemical Synthesis of Functionalized trans-Cyclooctenes Driven by Metal Complexation” J. Am. Chem. Soc. 2008, 130, 3760–3761.
30) DeAngelis, A.; Panne, P.; Yap, G. P. A.; Fox, J. M. “Rh-Catalyzed Formation of Dioxolanes from a-Alkyl Diazoesters: Diastereoselective Cycloadditions of Carbonyl Ylides with Selectivity over b-Hydride Elimination” J. Org. Chem. 2008, 73, 1435-1439.
29) Yan, N.; Liu, X.; Fox, J. M. “Facially Selective and Regioselective Carbometalation of Cyclopropenes by Aryl Grignard Reagents” J. Org. Chem. 2008, 73, 563-568.
28) Pallerla, M. K.; Fox, J. M. “Enantioselective Synthesis of (–)-Pentalenene” Org. Lett. 2007, 9, 5625-5628.
27) Dong, Z.; Yap, G. P. A.; Fox, J. M. “trans-Cyclohexane-1,2-diamine is a Weak Director of Absolute Helicity in Chiral Nickel-Salen Complexes” J. Am. Chem. Soc. 2007, 129, 11850-11853.
26) Panne, P.; Fox, J. M. “Rh-catalyzed Intermolecular Reactions of Alkynes withα-Diazoesters that Possessβ-hydrogens: Ligand-based Control over Divergent Pathways” J. Am. Chem. Soc. 2007, 129, 22-23.
25) Dong, Z.; Liu, X.; Yap, G. P. A.; Fox, J. M. “Two-Dimensional Scaffolds for the Parallel Alignment of Rod-Shaped Conjugated Molecules” J. Org. Chem. 2007, 72, 617-625.
24) Dong, Z.; Karpowicz, R. J. Jr. (undergraduate); Bai, S.; Yap, G. P. A.; Fox, J. M. “Control of Absolute Helicity in Single-Stranded Abiotic Metallofoldamers” J. Am. Chem. Soc. 2006, 128, 14242-14243.
23) Zhang, F.; Fox, J. M. “Synthesis of Cyclopropene a-Amino Acids by Enantioselective Desymmetrization” Organic Letters 2006, 8, 2965-2968.
22) Liu, X.; Fox, J. M. “Enantioselective, Facially Selective Carbomagnesation of Cyclopropenes” J. Am. Chem. Soc. 2006, 128, 5600-5601.
21) Yang, Z.; Xie, X.; Fox, J. M. “Diastereoselective Synthesis of Methylenecyclopropanes from Chiral Cyclopropene Derivatives” Angew. Chem. Int. Edit. 2006, 45, 3960-3962.
20) Pallerla, M. K.; Fox, J. M. “Diastereoselective Intermolecular Pauson Khand Reactions of Chiral Cyclopropenes” Organic Letters 2005, 7, 3593-3596.
19) Zhang, F.; Bai, S.; Yap, G. P. A.; Tarwade, V.; Fox, J. M. “Abiotic Metallofoldamers as Electrochemically Responsive Molecules” J. Am. Chem. Soc. 2005, 127, 10590-10599.
18) Fox, J. M.; Yan, N. “Metal Mediated and Catalyzed Nucleophilic Additions to Cyclopropenes” Current Organic Chemistry 2005, 9, 719-732. (Invited Contribution).
17) Liao, L.-a.; Yan, N.; Fox, J. M. “The Dianion Approach to Chiral Cyclopropene Carboxylic Acids” Organic Letters 2004, 6, 4937-4939.
16) Fox, J. M.; Dmintrenko, O.; Liao, L.-a.; Bach. R. D. “Computational Studies of Nucleophilic Substitution at Carbonyl Carbon: Applications to Organic Synthesis” J. Org. Chem. 2004, 69, 7317-7328.
15) Stone, M. T.; Fox, J. M.; Moore, J. S. “A Helicene-Containing Foldamer Displaying Highly Solvent Dependent CD Spectra” Org. Lett. 2004, 6, 3317-3320.
14) Liao, L.-a.; Zhang. F.; Dmintrenko, O.; Bach, R. D.; Fox, J. M. “A Reactivity/Affinity Switch for Parallel Kinetic Resolution: a-Amino Acid Quasienantiomers and the Resolution of Cyclopropene Carboxylic Acids” J. Am. Chem. Soc. 2004, 126, 4490-4491.
13) Liao, L.-a.; Zhang, F.; Yan, N.; Golen, J. A.; Fox, J. M. “An Efficient and General Method for Resolving Cyclopropene Carboxylic Acids” Tetrahedron 2004, 1803-1816.
12) Liao, L.-a.; Fox,
J. M. "A Copper-catalyzed Method for the Facially Selective Addition of
Grignard Reagents to Cyclopropenes" J. Am. Chem. Soc. 2002, 124,
14322–14323.
11) Kaye, S. (undergraduate mentored by Fox); Fox, J. M.; Hicks, F. A.; Buchwald, S. L. "The Use of Catalytic Amounts of CuCl and Other Improvements in the Benzyne Route to Biphenyl-Based Ligands" Adv. Synth. Catal. 2001, 343, 789.
10) Chieffi, A.; Kamikawa, K.; Åhman, J.; Fox, J. M. "Catalytic Asymmetric Vinylation of Ketone Enolates" Org. Lett. 2001, 3, 1897-1900
9) Tomori, H.; Fox, J. M.; Buchwald, S. L. "An Improved Synthesis of Functionalized Biphenyl-Based Phosphine Ligands" J. Org. Chem. 2000, 65, 5334
8) Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. "Highly Active and Selective Catalysts for the Formation of a-Aryl Ketones" J. Am. Chem. Soc. 2000, 122, 1360.
7) Buchwald, S. L.; Fox, J. M. "Recent Progress in the Suzuki Reactions of Aryl Chlorides" Strem Chemiker 2000 Vol. XVIII No. 1.
6) Fox, J. M.; Katz, T. J.; Van Elschocht, S.; Verbiest, T.; Kauranen, M.; Persoons, A.; Thongpanchang, T.; Krauss, T.; Brus, L. "Synthesis, Self-Assembly, and Nonlinear Optical Properties of Conjugated Helical Metal Phthalocyanine Derivatives" J. Am. Chem. Soc. 1999, 121, 3454.
5) Fox, J. M.; Katz, T. J. "Conversion of a [6]Helicene into an [8]Helicene and a Helical 1,10-Phenanthroline Ligand" J. Org. Chem. 1999, 64, 302
4) Fox, J. M.; Goldberg, N. R. (undergraduate mentored by Fox); Katz, T. J. "Efficient Synthesis of Functionalized [7]Helicenes" J. Org. Chem. 1998, 63, 7456
3) Fox, J. M.; Lin, D. (undergraduate mentored by Fox); Itagaki, Y.; Fujita, T. "Synthesis of Conjugated Helical Acetylene-Bridged Polymers and Cyclophanes" J. Org. Chem. 1998, 63, 2031.
2) Katz, T. J.; Liu, L.; Willmore, N. D.; Fox, J. M.; Rheingold, A. L.; Shi, S.; Nuckolls, C.; Rickman, B. H. "An Efficient Synthesis of Functionalized Helicenes" J. Am. Chem. Soc. 1997, 119, 10054.
1) Fox, J. M.; Scacheri Gillen, J. E.; Jones, K. J. L.; Jones, M., Jr.; Shevlin, P. B.; Armstrong, B.; Sztyrbicka, R. "The Phenylcarbene Rearrangement as a Source of Real Carbenes" Tetrahedron Lett. 1992, 33, 5021.
46) USC Department of Radiology, Keck School of Medicine, October 29,2010.
45) University of Houston, Department of Chemistry, October 12, 2010.
44) University of South Florida, Department of Chemistry, November 19, 2009.
43) Hunter College, Department of Chemistry, October 23, 2009.
42) University of Kansas, Department of Chemistry, November 14, 2008.
41) Colorado State University, Department of Chemistry, November 10, 2008.
40) Florida State University, Department of Chemistry and Biochemistry, May 1, 2008.
39) National Institutes of Health, NIH Chemistry Seminar Series, Bethesda MD, February 21, 2008.
38) Astra Zeneca, Wilmington DE, January 24, 2008.
37) City College of New York, Department of Chemistry, November 12, 2007.
36) Smith College, Department of Chemistry, March 5, 2007.
35) University of New Mexico, Department of Chemistry, March 30, 2007.
34) West Virginia University, Department of Chemistry, January 31, 2007.
33) Johns-Hopkins University, Department of Chemistry, October 17, 2006.
32) New York University, Department of Chemistry, November 6,2006.
31) Symyx Technologies, San Jose CA, December 1, 2006.
30) Wayne State University, Department of Chemistry, May 17, 2006.
29) University of Michigan, Department of Chemistry, May 16, 2006.
28) Michigan State University, Department of Chemistry, May 15, 2006.
27) University of Pittsburgh, Department of Chemistry, April 20, 2006.
26) Princeton University, Department of Chemistry, March 7, 2006.
25) Salisbury University, Department of Chemistry, March 3, 2006.
24) Columbia University, Department of Chemistry, February 16, 2006.
23) Northwestern University, Eli Lilly Organic Seminar Series Speaker. February 6, 2005.
22) University of North Carolina at Chapel Hill, Department of Chemistry, January 26, 2006.
21) Wake Forest University, Department of Chemistry, January 25, 2006.
20) California Institute of Technology, Division of Chemistry and Chemical Engineering, January 18, 2006.
19) Brown University, December 9, 2005.
18) Duke University, Department of Chemistry, November 11, 2005.
17) University of Rochester, Department of Chemistry, November 4, 2005.
16) SUNY Buffalo, Department of Chemistry and Medicinal Chemistry, November 3, 2005.
15) George Washington University, Department of Chemistry, October 28, 2005.
14) University of Illinois at Chicago, Department of Chemistry, August 30, 2005.
13) Incyte Corporation, Wilmington DE. August 24, 2005.
12) University of Missouri. Plenary Lecturer at annual statewide organic chemistry symposium. April 16, 2005.
11) Merck and Co., Inc., Process Research Division Rahway, NJ. March 2005.
10) Philadelphia Organic Chemists Club, University of Pennsylvania, January 27, 2005.
9) DuPont Stine-Haskell Research Center, November 1, 2004.
8) James Madison University, Harrisonburg, VA. Departmental Seminar, October 22, 2004.
7) University of Minnesota, Minneapolis, Minn. Organic Division Seminar, October 1, 2004.
6) Rutgers University, New Brunswick, NJ. Departmental Colloquium, May 4, 2004.
5) Temple University, Philadelphia, PA. Departmental Seminar, November 20, 2003.
4) The College of New Jersey, Trenton, NJ. Departmental Seminar, October 2, 2003.
3) Shepherd College, Shepherdstown, WV 25443. Seminar, September 22, 2003.
2) Rider University, Departmental Seminar, Fall 2002.
1) University of the Sciences in Philadelphia, Philadelphia, PA, 19104. Departmental Seminar, October, 2001.
Chem 331 Organic Chemistry I for majors. 2002F
Chem 332 Organic Chemistry II for majors. 2003S; 05S; 06S; 07S; 08S; 09S; 10S
Chem 333 Introduction to Spectroscopic Structure Determination. 2001F, 2009F
Chem 334 Laboratory for Organic Chemistry II. 2003S; 05S; 06S; 07S; 08S; 09S; 10S
Chem 634 Advanced Organic Chemistry–Synthesis and Reactivity2004S, 04F, 05F,
Chem 635 Topics in Total Synthesis