`
`Gojko Lalic
`
`Department of Chemistry
`University of Washington
`Box 351700
`Seattle, WA 98195-1700
`lalic@chem.washington.edu
`
`304H Chemistry Building
`206.616.8493
`fax 206.685.8665
`http://faculty.washington.edu/lalic/
`http://depts.washington.edu/chem/people/faculty/lalic.html
`
`EDUCATION
`
`Ph.D., Organic Chemistry, Harvard University
`Thesis: Enantioselective metal-catalyzed thioester aldol and Mannich reactions
`Advisor: Professor Matthew D. Shair
`
`B.S., Chemistry, University of Belgrade
`Advisor: Professor Radomir N. Saicic
`
`RESEARCH EXPERIENCE
`
`Assistant Professor
`Department of Chemistry, University of Washington
`Developing new transformations for organic synthesis
`
`Postdoctoral Research Fellow
`Department of Chemistry & Chemical Biology, Harvard University
`Enantioselective synthesis of platensimycin core
`Advisor: Professor E.J. Corey
`
`1998–2004
`
`1993–1998
`
`2008–present
`
`2006–2008
`
`Postdoctoral Research Fellow
`Department of Chemistry, University of California at Berkeley
`Substitution reactions of monomeric zirconium imido and zirconium oxo complexes
`Advisor: Robert G. Bergman
`
`2004–2006
`
`1998–2004
`
`Summer 1997
`
`Graduate Research Assistant
`Department of Chemistry & Chemical Biology, Harvard University
`Enantioselective metal-catalyzed thioester aldol and Mannich reactions
`Advisor: Prof. Matthew D. Shair
`
`Undergraduate Research Assistant
`Department of Chemistry, Texas A&M University
`Selective functionalization of saturated hydrocarbons
`Advisor: Professor Derek H. R. Barton
`
`HONORS AND AWARDS
`
`2013–2018 CAREER Award, National Science Foundation
`2002–2003
`Eli Lilly Predoctoral Fellowship, Harvard University
`2002
`Certificate of Distinction in Teaching, Harvard University
`1999–2000
`Eli Lilly Predoctoral Fellowship, Harvard University
`
`Gojko Lalic
`
`Curriculum Vitae
`
`1 of 7
`
`PARAGON - EXHIBIT 2017
`
`

`

`
`
`1998
`
`Vojislav Stojanovic Award for Outstanding Academic Achievement, University
`of Belgrade, Serbia
`
`1995–1998
`
`Fellowship for Talented Students in Sciences and Arts, Ministry of Science,
`Serbia
`
`PUBLICATIONS (all peer-reviewed)
`
`30. Cox, N.; Whittaker, A. M.; Lalic, G. “Copper-catalyzed semi-reduction of alkynes.”
`Organic Syntheses (invited manuscript in review).
`
`29. Dang, H.; Whittaker, A. M.; Lalic, G. “Catalytic Activation of a Single C-F Bond in
`Trifluoromethyl Arenes.” Chem. Sci. Advanced Article DOI: 10.1039/C5SC03415A.
`
`28.
`
`Suess, A. M.; Uehling, M. R.; Kaminsky, W.; Lalic, G. “Mechanism of Copper-Catalyzed
`Hydroalkylation of Alkynes: An Unexpected Role of Dinuclear Copper Complexes.” J.
`Am. Chem. Soc. 2015, 137, 7747−7753. DOI: 10.1021/jacs.5b03086
`
`27. Mailig, M.; Rucker, R. P.; Lalic, G. “Practical Catalytic Method for Synthesis of Sterically
`Hindered Anilines.” Chem. Comm. 2015, 51, 11048–11051. DOI: 10.1039/c5cc03565a
`
`26. Uehling, M. R.; Suess, A. M.; Lalic, G. “Copper-Catalyzed Hydroalkylation of Terminal
`Alkynes.” J. Am. Chem. Soc. 2015, 137, 1424–1427. DOI: 10.1021/ja5124368
`
`25. Uehling, M. R.; Rucker, R. P.; Lalic, G. “Catalytic Anti-Markovnikov Hydrobromination
`of Alkynes.” J. Am. Chem. Soc. 2014, 136, 8799–8803. DOI: 10.1021/ja503944n
`
`24. Dang, H.; Mailig, M.; Lalic, G. “Mild Copper-Catalyzed Fluorination of Alkyl Triflates
`with Potassium Fluoride.” Angew. Chem., Int. Ed. 2014, 53, 6473–6476. DOI:
`10.1002/anie.201402238
`
`23. Cox, N.; Dang, H.; Whittaker, A. M.; Lalic, G. “NHC-copper hydrides as chemoselective
`reducing agents: catalytic reduction of alkynes, alkyl triflates, and alkyl halides.”
`2014,
`70
`(27-28),
`4219–4231.
`(Invited
`article)
`DOI:
`Tetrahedron
`10.1016/j.tet.2014.04.004
`
`22. Dang, H.; Cox, N.; Lalic, G. “Copper-Catalyzed Reduction of Alkyl Triflates and Iodides:
`An Efficient Method for the Deoxygenation of Primary and Secondary Alcohols.” Angew.
`Chem., Int. Ed. 2014, 53, 752–756. DOI: 10.1002/anie.201307697
`
`21. Cox, N.; Uehling, M. R.; Haelsig, K. T.; Lalic, G. “Catalytic Asymmetric Synthesis of
`Cyclic Ethers Containing an α-Tetrasubstituted Stereocenter.” Angew. Chem., Int. Ed.
`2013, 52, 4878–4882. (Highlighted in SYNFACTS) DOI: 10.1002/anie.201300174
`
`the Selective
`20. Whittaker, A. M.; Lalic, G. “Monophasic Catalytic System for
`Semireduction of Alkynes.” Org. Lett. 2013, 15, 1112–1116. (Highlighted
`in
`SYNFACTS) DOI: 10.1021/ol4001679
`
`19. Rucker, R. P.; Lalic, G. “Copper-Catalyzed Electrophilic Amination of Organoboron
`Compounds.” Synlett 2013, 24 (3), 269–274. (Invited SYPACTS article). DOI: 10.1055/s-
`0032-1317744
`
`18. Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. “Synthesis of Tertiary Alkyl Amines
`from Terminal Alkenes: Copper-Catalyzed Amination of Alkyl Boranes.” J. Am. Chem.
`Soc. 2012, 134, 6571–6574. (Highlighted in SYFACTS) DOI: 10.1021/ja3023829
`
`Gojko Lalic
`
`Curriculum Vitae
`
`2 of 7
`
`

`

`
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`17. Rucker, R. P.; Whittaker, A. M.; Dang, H.; Lalic, G. “Synthesis of Hindered Anilines:
`Copper-Catalyzed Electrophilic Amination of Aryl Boronic Esters.” Angew. Chem., Int.
`Ed. 2012, 51, 3953–3956. (Highlighted in SYNFACTS) DOI: 10.1002/anie.201200480
`
`16. Uehling, M. R.; Marionni, S. T.; and Lalic, G. “Asymmetric Synthesis of Trisubstituted
`Allenes: Copper-Catalyzed Alkylation and Arylation of Propargylic Phosphates.” Org.
`Lett. 2012, 14, 362–365. DOI: 10.1021/ol2031119
`15. Whittaker, A. M.; Rucker, R. P.; Lalic, G. “Catalytic SN2′-Selective Substitution of Allylic
`Chlorides with Arylboronic Esters.” Org. Lett. 2010, 12, 3216–3218. (Highlighted in
`SYNFACTS) DOI: 10.1021/ol101171v
`
`Prior to the University of Washington
`
`14. Lalic, G.; Corey, E. J. “Enantioselective Rhodium(I)-Triethylamine Catalyzed Addition of
`Potassium Isopropenyltrifluoroborate to Enones.” Tetrahedron Lett. 2008, 49 (33), 4894-
`4896. DOI: 10.1016/j.tetlet.2008.05.147
`13. Lalic, G.; Krinsky, J. L.; Bergman, R. G. “The Scope and the Mechanism of SN2′
`Substitution Reactions of a Monomeric Imidozirconium Complex With Allylic
`Electrophiles.” J. Am. Chem. Soc. 2008, 130, 4459–4465. DOI: 10.1021/ja7106096
`
`12. Lalic, G.; Corey, E. J. “An Effective Enantioselective Route to the Platensimycin Core.”
`Org. Lett. 2007, 9, 4921–4923. DOI: 10.1021/ol702323s
`
`11.
`
`Fox, R. J.; Lalic, G.; Bergman, R. G. “Regio- and Stereospecific Formation of Protected
`Allylic Alcohols via Zirconium-Mediated SN2′ Substitution of Allylic Chlorides.” J. Am.
`Chem. Soc. 2007, 129, 14144–14145. DOI: 10.1021/ja075967i
`10. Lalic, G.; Blum, S. A.; Bergman, R. G. “Zirconium-Mediated SN2′ Substitution of Allylic
`Ethers: Regio- and Stereospecific Formation of Protected Allylic Amines.” J. Am. Chem.
`Soc. 2005, 127, 16790–16791. DOI: 10.1021/ja056132f
`
`9. Magdziak, D.; Lalic, G.; Lee, H.-M.; Fortner, K. C.; Aloise, A. D.; Shair, M. D. “Catalytic
`Enantioselective Thioester Aldol Reactions That are Compatible With Protic Functional
`Groups.” J. Am. Chem. Soc. 2005, 127, 7284–7285. DOI: 10.1021/ja051759j
`
`8.
`
`7.
`
`6.
`
`5.
`
`4.
`
`Xu, K.; Lalic, G.; Sheehan, S. M.; Shair, M. D. “Dynamic Kinetic Resolution During a
`Cascade Reaction on Substrates with Chiral All-Carbon Quaternary Centers.” Angew.
`Chem., Int. Ed. 2005, 44, 2259–2261. DOI: 10.1002/anie.200462039
`
`Lalic, G.; Aloise, A. D.; Shair, M. D. “An Exceptionally Mild Thioester Aldol Reaction
`Inspired by Polyketide Biosynthesis.” J. Am. Chem. Soc. 2003, 125, 2852–2853. DOI:
`10.1021/ja029452x
`
`Burke, M. D.; Lalic, G. “Teaching Target-Oriented and Diversity-Oriented Organic
`Synthesis at Harvard University.” Chem. Biol. 2002, 9, 535–541. DOI: 10.1016/S1074-
`5521(02)00143-6
`
`Korbel, G. A.; Lalic, G.; Shair, M. D. “Reaction Microarrays: A Method for Rapidly
`Determining the Enantiomeric Excess of Thousands of Samples.” J. Am. Chem. Soc. 2001,
`123, 361–362. DOI: 10.1021/ja0034747
`
`Lalic, G.; Petrovski, Z.; Galonic, D.; Matovic, R.; Saicic, R. N. “Alkylation of Carbonyl
`Compounds in the TiCl4-promoted Reaction of Trimethylsilyl Enol Ethers with
`Epoxides.” Tetrahedron 2001, 57 (3), 583–591. DOI: 10.1016/S0040-4020(00)01028-0
`
`Gojko Lalic
`
`Curriculum Vitae
`
`3 of 7
`
`

`

`
`
`3.
`
`2.
`
`1.
`
`Sheehan, S. M.; Lalic, G.; Chen, J. S.; Shair, M. D. “A Highly Efficient and Convergent
`Reaction for the Synthesis of Bridgehead Enone-Containing Polycyclic Ring Systems.”
`Ed.
`2000,
`39,
`2714-2715. DOI:
`10.1002/1521-
`Angew. Chem.,
`Int.
`3773(20000804)39:15<2714::AID-ANIE2714>3.0.CO;2-1
`
`Lalic, G.; Petrovski, Z.; Galonic, D.; Matovic, R.; Saicic, R. N. “Alkylation of Carbonyl
`Compounds in the TiCl4-promoted Reaction of Trimethylsilyl Enol Ethers with Ethylene
`Oxide.” Tetrahedron Lett. 2000, 41 (5), 763–766. DOI: 10.1016/S0040-4039(99)02149-8
`
`Barton, D. H. R.; Lalic, G.; Smith, J. A. “The Selective Functionalization of Saturated
`Hydrocarbons. Part 42. Further Studies in Selective Phenylselenation.” Tetrahedron 1998,
`54 (9), 1725–1734. DOI: 10.1016/S0040-4020(97)10397-0
`
`PATENTS
`1. Method for Analysis of Reaction Products. Matthew D. Shair; Gregory A. Korbel; Gojko
`Lalic, U.S. Patent Appl. 09/778,708, February 7, 2001.
`
`INVITED LECTURES
`
`24. Heterocycles Compounds Gordon Research Conference, Salve Regina University,
`Newport, RI, June 2016 (scheduled).
`
`23.
`
`Johnson & Johnson Pharmaceutical Research & Development, San Diego, CA, June 18,
`2015.
`22. Gilead Sciences, Foster City, CA, May 12, 2015.
`21. AbbVie, Worcester, MA, April 30, 2015.
`
`20. Department of Chemistry, University of Illinois‒Urbana-Champaign, IL, November 13,
`2014.
`
`19. Organic Reactions & Processes Gordon Research Conference, Bryant University,
`Smithfield, RI, July 18, 2014.
`
`18. Organometallic Chemistry Gordon Research Conference, Salve Regina University,
`Newport, RI, July 8, 2014
`
`17. Department of Chemistry, University of California‒Berkeley, Berkeley, CA, April 8,
`2014.
`16. Department of Chemistry, Duke University, Durham, NC, September 20, 2013.
`
`15. Department of Chemistry, University of North Carolina‒Chapel Hill, Chapel Hill, NC,
`September 19, 2013.
`15. The Scripps Research Institute, La Jolla, CA, June 5, 2013.
`
`14. Department of Chemistry, University of California‒Irvine, Irvine, CA, June 4, 2013.
`13. Department of Chemistry, Princeton University, Princeton, NJ, May 28, 2013.
`12. Department of Chemistry, Stanford University, Stanford, CA, May 14, 2013.
`11. Department of Chemistry, Northwestern University, Evanston, IL, April 12, 2013.
`
`10. Department of Chemistry, University of Illinois‒Chicago, Chicago, IL, April 11, 2013.
`
`9.
`
`Department of Chemistry & Biochemistry, University of Texas‒Austin, Austin, TX,
`March 27, 2013.
`
`Gojko Lalic
`
`Curriculum Vitae
`
`4 of 7
`
`

`

`
`
`8.
`7.
`6.
`
`5.
`
`4.
`
`3.
`
`2.
`
`1.
`
`Department of Chemistry, University of Houston, Houston, TX, March 26, 2013.
`Department of Chemistry, Boston College, Chestnut Hill, MA, February 26, 2013.
`Department of Chemistry, University of Chicago, Chicago, IL, November 30, 2012.
`
`Department of Chemistry, Bowling Green State University, Bowling Green, OH,
`September 20, 2012.
`Department of Chemistry, Wayne State University, Detroit, MI, September 19, 2012.
`
`Department of Chemistry & Biochemistry, The Ohio State University, Columbus, OH,
`September 18, 2012.
`
`Department of Chemistry & Biochemistry, University of Delaware, Newark, DE,
`September 5, 2012.
`Department of Chemistry, Yale University, New Haven, CT, September 4, 2012.
`
`GRANTS
`
`Awarded
`05/2013-05/2018
`National Science Foundation (PI)
`CAREER: Catalytic Methods for Hydrofunctionalization of Unsaturated Compounds
`
`University of Washington (PI)
`Royalty Research Fund
`Catalytic Anti-Markovnikov Hydroamination and Hydrocyanation of Alkenes
`
`06/2012-06/2013
`
`$650,000
`
`$37,605
`
`Not Awarded
`2014 NSF CHE 1464510 Transition metal catalyzed reactions of organofluorine compounds
`
`2014 NIH 1R01GM112849-01 Transition metal catalyzed reactions of organofluorine
`compounds
`2010 NIH 1R01GM097307-01 Copper-catalyzed reactions of organoboron compounds
`
`2011 NIH 1R01GM099816-01 Copper-Catalyzed Functionalization of Organoboron
`Compounds
`
`2011 NIH 1R01GM102421-01 New Organic Reactions Catalyzed by Late Transition Metal
`Complexes
`
`PROFESSIONAL ACTIVITIES
`
`Journal Reviews
`Angewandte Chemie
`Journal of the American Chemical Society
`Nature Chemistry
`Organic Letters
`Chemical Science
`ACS Catalysis
`Chemical Communications
`Journal of Organic Chemistry
`
`
`
`Gojko Lalic
`
`Curriculum Vitae
`
`5 of 7
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`

`

`
`
`Department Service
`Chemistry Research Laboratory Safety Committee, 2009–2011
`Chemistry Graduate Recruiting Committee, 2008–present
`Chemistry Graduate Exam Committees, 2008–present
`Chemistry Sophomore-level Organic Taskforce, 2008–2011
`
`MENTORING
`
`Current Ph.D. Students
`Nathan Gelman
`06/2015-present
`Mitchell Lee
`06/2015-present
`Bingyan Mei
`01/2015-present
`Julia Nguyen
`01/2015-present
`Mary Nguyen
`01/2015-present
`Melrose Mailig
`1/2013–present
`Hester Dang
`1/2011–present
`
`Dissertations Supervised
`
`Mycah Uehling
`
`Nick Cox
`
`Richard Rucker
`
`Aaron Whittaker
`
`Ph.D. Chemistry, June 2015
`Thesis Gold-Catalyzed Asymmetric Synthesis of Cyclic Ethers and
`Copper-Catalyzed Hydrofunctionalization of Alkynes
`Current Postdoctoral researcher with Stephen Buchwald, Massachusetts
`Institute of Technology
`
`Ph.D. Chemistry, December 2013
`Thesis Development of Practical Synthetic Tools Using Copper and
`Gold Catalysis
`Current Postdoctoral researcher with Chaitan Khosla & Mark Smith,
`Medicinal Chemistry Knowledge Center, Chemistry,
`Engineering & Medicine for Human Health (ChEM-H), Stanford
`University
`
`Ph.D. Chemistry, December 2013
`Thesis Copper-Catalyzed Reactions of Organoboron Compounds
`Current Scientist, Polymer Science & Materials Chemistry, Exponent
`Previous Postdoctoral researcher with Michael Organ, York University
`
`Ph.D. Chemistry, August 2013
`Thesis New Copper-Catalyzed Reactions of Organoboron and
`Organosilicon Compounds
`Current Senior Scientist, Process research and development, Merck
`Previous Postdoctoral researcher with Vy Dong, University of California–
`Irvine
`
`Former Postdoctoral Researchers
`
`Dr. Alison Suess
`
`11/2013–4/2015
`
`
`
`
`
`Gojko Lalic
`
`Curriculum Vitae
`
`6 of 7
`
`

`

`
`
`Former Long-term Researchers
`
`Stephen Carlin
`Samuel Marionni
`Benjamin Burrone
`Derek Whorton
`
`2013-2014
`2010-2011
`2010
`2009
`
`Former Undergraduate Researchers
`
`Tyler Mann
`Karl Haelsig
`
`2008
`2012–2015
`
`M.S. 2015
`Current Ph.D. student with Matthew Bush (Chemistry)
`M.S. 2011
`M.S. 2009
`
`(co-author, Angew. Chem. Int. Ed. 2013, 52, 4878-4882)
`
`Student Awards
`
`Stephen Carlin
`Nick Cox
`Samuel Marionni
`Mary Nguyen
`Richard Rucker
`Mycah Uehling
`Aaron Whittaker
`
`TEACHING
`
`2013 Arthur G. Andersen Endowed Graduate Fellowship
`2012-13 Outstanding Teaching Assistant Award
`2009 Klaus and Mary Ann Saegebarth Endowed Graduate Fellowship
`2014 Basil G. and Gretchen F. Anex Endowed Graduate Fellowship
`2008 Tomas Hirschfeld Endowed Graduate Fellowship
`2013 Amy Scott and Stephen C. Alley Endowed Graduate Fellowship
`2012 Gary and Sue Christian Endowed Graduate Fellowship
`
`
`CHEM 237 Organic Chemistry (Undergraduate)
`
`Summer Quarter 2015
`CHEM 238 Organic Chemistry (Undergraduate)
`
`Winter Quarter 2015
`CHEM 224: Organic Chemistry–Short Program (Undergraduate)
`
`Winter Quarter 2012, 2013
`CHEM 337: Honors Organic Chemistry (Undergraduate)
`
`Spring Quarter 2009, 2010, 2011
`CHEM 530: Advanced Organic Chemistry (Graduate)
`
`Autumn Quarter 2008, 2009, 2010, 2011, 2012, 2013, 2014
`CHEM 593: Seminar in Organic Chemistry (Graduate)
`
`Autumn, Winter, Spring Quarters 2008-2009 (coordinator)
`
`
`Gojko Lalic
`
`Curriculum Vitae
`
`7 of 7
`
`