Elizabeth R. JarvoAssistant Professor, Chemistry |
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| URL | For up to date information, please see Jarvo Group Website | |
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Academic Distinctions |
Thieme Chemistry Journal Award (2010) UCI School of Physical Sciences Outstanding Contributions to Undergraduate Education Award (2009) NSF CAREER Award (2009) PRF-Type G Award (2006) Lilly New Faculty Award (2005) Amgen New Faculty Award (2005) NSERC Postgraduate Scholarship (1997, Declined) |
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| Appointments | Postdoctoral Fellow, Harvard University, 2002-2005 | |
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Research Abstract |
Please see the Jarvo group website for a more detailed description and links to our publications: http://chem.ps.uci.edu/~erjarvo/ Catalysts play a critical role in synthetic organic chemistry. The right catalyst can control a reaction's chemoselectivity and stereoselectivity, providing an efficient route to the required product. Many elegant syntheses of biologically active compounds rely on highly selective catalytic transformations for streamlined assembly of the required functional groups. The focus of our research interests is the development of new reactions using organometallic catalysts, and application of these transformations in complex target-oriented synthesis. In addition to providing valuable synthetic methods, these studies test and deepen our understanding of the fundamental principles that underlie reactivity. Palladium- and silver-catalyzed additions to electrophiles We have described a new class of nucleophilic allylpalladium complexes with bidentate neutral N-heterocyclic carbene (NHC) ligands. We have used these complexes to develop catalytic allylation reactions of imines and conjugate acceptors including N-acylpyrroles. We have used the mechanistic insight gained in these studies to develop cascade reactions and enantioselective approaches to propargylation reactions of electrophiles. Nickel-catalyzed amination and alkyl-alkyl cross-coupling reactions Nickel catalysts are versatile in that they have the ability to participate in both radical and polar mechanisms for oxidative addition. Two transformations developed by examining new oxidative addition partners have been developed in our group. Nickel-catalyzed, NCS-mediated coupling of amines with organozinc reagents affords an umpolung approach to amination reactions. Stereospecific cross-coupling reactions of ethers provide synthetic access to enantioenriched diarylethanes. Collaboration to test compounds for selective activity against cancer cell lines Many of the compounds that we synthesize over the course of developing new catalytic reactions are structurally related to medicinal agents with proven biological activity. We collaborate with the research group of Professor Zi, UC Irvine Medical School, to test these new compounds for growth inhibitory effect against prostate, bladder, and ovarian cancer cell lines. |
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| Publications | (21) “Palladium-Catalyzed Cascade Reaction for Synthesis of Substituted Isoindolines” F. J. Williams, E. R. Jarvo Angew. Chem. Int. Ed. A. S. A. P. | |
| (20) “Enantioselective Silver-Catalyzed Propargylation Reactions of Imines" H. M. Wisniewska, E. R. Jarvo Chemical Science, 2011, 2, 807-810. | ||
| (19) “Stereospecific Nickel-Catalyzed Cross-Coupling Reactions of Alkyl Ethers: Enantioselective Synthesis of Diarylethanes” B. L. Taylor, E. C. Swift, J. D. Waetzig, E. R. Jarvo J. Am. Chem. Soc. 2011, 133, 389. | ||
| (18) “Diene-Ligated Iridium Complexes as Catalysts for Allylation and Methallylation Reactions of Ketones” T. J. Barker, E. R. Jarvo Synthesis 2010, 19, 3259-3262. | ||
| (17) “Umpolung Amination: Nickel-Catalyzed Coupling Reactions of N,N-Dialkyl-N-chloroamines with Diorganozinc Reagents” T. J. Barker, E. R. Jarvo, J. Am. Chem. Soc. 2009, 131, 15598-15599 | ||
| (16) “Diene-Ligated Iridium Catalyst for Allylation Reactions of Ketones and Imines” T. J. Barker, E. R. Jarvo, Org. Lett. 2009, 11, 1047-1049. | ||
| (15) “Palladium-Catalyzed, One-Pot, Three-Component Synthesis of Homoallylic Amines from Aldehyde Anisidine, and Allyl Trifluoroacetate” R. E. Grote, E. R. Jarvo, Org. Lett. 2008,11, 485-488. | ||
| (14) “Conjugate Allylation Reactions of Alkylidene Malonitriles Catalyzed by NHC-ligated Palladium Catalysts.” J.D. Waetzig, E.C. Swift, E.R. Jarvo, Tetrahedron, 2009, 65, 3197-3201. | ||
| (13) “Silver-Catalyzed, Manganese-Mediated Allylation Reactions of Aldehydes and Ketones.” N.T. Barczak, E.R. Jarvo, Eur. J. Org. Chem., 2008, 5507-5510. | ||
| (12) “Palladium-Catalyzed Conjugate Allylation of a,b-Unsaturated N-Acylpyrroles.” M.B. Shaghafi, B.L. Kohn, E.R. Jarvo, Org. Lett., 2008, 10, 4743-4746. | ||
| (11) “Catalytic Umpolung Allylation of Aldehydes by pi-Allylpalladium Complexes Containing Bidentate N-Heterocyclic Carbene Ligands.” N.T. Barczak, R.E. Grote, E.R. Jarvo, Organometallics, 2007, 26, 4863-4865 | ||
| (10) “Efficient Total Syntheses of (-)-Colombiasin A and (-)-Elisapterosin B: Application of the Cr-Catalyzed Asymmetric Quinone Diels-Alder Reaction." A. A. Boezio, E.R. Jarvo, B.M. Lawrence, E.N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 6046-6050. | ||
| (9) “Highly Enantio- and Regioselective Quinone Diels-Alder Reaction Catalyzed by a Tridentate [(Schiff Base)CrIII] Complex.” E.R. Jarvo, B.M. Lawrence, E.N. Jacobsen, Angew. Chem. Int. Ed. 2005, 44, 6043-6046. | ||
| (8) “Asymmetric Acylations.” E.R. Jarvo and S.J. Miller, Comprehensive Asymmetric Catalysis, Supplement 1; Jacobsen, E.N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, Heidelberg, 2004; Chapter 43. | ||
| (7) “Amino Acids and Peptides as Asymmetric Organocatalysts.” E.R. Jarvo and S.J. Miller, Tetrahedron, 2002, 58, 2481-2495. | ||
| (6) “Fluorescence-Based Screening of Asymmetric Acylation Catalysts Through Parallel Enantiomer Analysis. Identification of a Catalyst for Tertiary Alcohol Resolution.” E.R. Jarvo, C. A. Evans, G.T. Copeland, S.J. Miller. J. Org. Chem. 2001, 66, 5522-5527. | ||
| (5) “Incorporation of Peptide Isosteres into Enantioselective Peptide-Based Catalysts as Mechanistic Probes.” M.M. Vasbinder, E.R. Jarvo, S.J. Miller. Angew. Chem. Int. Ed. 2001, 40, 2824-2827. | ||
| (4) “Asymmetric Acylation Reactions Catalyzed by Conformationally Biased Octapeptides.” E.R. Jarvo, M.M. Vasbinder, S.J. Miller. Tetrahedron 2000, 56, 9773-9779. | ||
| (3) “A Biomimetic Approach to Asymmetric Acyl Transfer Catalysis.” E.R. Jarvo, G.T. Copeland, N. Papaioannou, P.J. Bonitatebus, Jr., and S.J. Miller J. Am. Chem. Soc. 1999, 121, 11638-11643. | ||
| (2) “Minimal Acylase-Like Peptides. Conformational Control of Absolute Stereospecificity.” G.T. Copeland, E.R. Jarvo and S. J. Miller. J. Org. Chem. 1998, 63, 6784-6785. | ||
| (1) “High-Pressure Diels-Alder Reactions of Quinone mono-ketals.” E.R. Jarvo, S.R. Boothroyd and M.A. Kerr. Synlett 1996, 879. | ||
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Professional Societies |
American Chemical Society Chao Family Comprehensive Cancer Center Iota Sigma Pi |
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| Link to this profile | http://www.faculty.uci.edu/profile.cfm?faculty_id=5279 | |
| Last updated | 04/13/2011 | |