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Robert E. Gawley CHEM 213 |
Degrees:
B.S., Stetson University, 1970
Ph.D., Duke University, 1975
Research Associate, University of North Carolina at Chapel Hill, 1975-77
Faculty, University of Miami, 1977-2002
Awards
Fogarty Senior International Fellow, ETH-ZÜrich, 1993-94
Provost's Award for Scholarly Activity, University of Miami, 2000-2001
Distinguished Alumnus Award, Stetson University, 2001
Fellow, American Association for the Advancement of Science, 2006
Fellow, Royal Society of Chemistry, 2006
Research Interests:
asymmetric synthesis and sensors
Research:
There are several areas of emphasis in my group: asymmetric synthesis using chiral organometallics; development of new synthetic methods; development of new sensors for marine toxins and other xenobiotics; natural products isolation and structure elucidation.
Publications/Presentations:
"Principles of Asymmetric Synthesis" R. E. Gawley and J. Aubé, volume 14 in the Tetrahedron Organic Chemistry Series, Elsevier (Pergamon imprint): Oxford, 1996.
"Stereoselective Addition of Chiral a-Aminorganometallics to Aldehydes" R. E. Gawley, in Advances in Asymmetric Synthesis, vol. 3, A. Hassner, ed., JAI: Stamford, CT, 1998, pp 77-111.
"Marine Toxins: How They are Studied and What They Can Tell Us" D. G. Baden; K. S. Rein; R. E. Gawley in Molecular Approaches to the Study of the Oceans, K. Cooksey, ed., Chapman and Hall: London, 1998, pp 487-514.
"A Proposal for (slight) Modification of the Hughes-Ingold Mechanistic Descriptors for Substitution Reactions" R. E. Gawley, Tetrahedron Lett., 1999, 40, 4297-4300.
"Anthracylmethyl Crown Ethers as Fluorescence Sensors of Saxitoxin" R. E. Gawley, Q. Zhang, P. I. Higgs, S. Wang, R. M. Leblanc, Tetrahedron Lett., 1999, 40, 5461-5465, corrigendum 6135.
"Unusual Conformational Effect in a-Aminoorganostannanes" R. E. Gawley; E. Low; G. Chambournier, Org. Lett. 1999, 1, 653-656.
"Stereoselective Additions of Chiral a-Amino Grignard Reagents to Aldehydes" R. E. Gawley, In Grignard Reagents - New Developments, H. Richey, Ed., John Wiley & Sons: New York, 2000, pp 139-164.
"Amphiphilic Anthracyl Crown Ether: A Langmuir and Langmuir-Blodgett Film Study" S. Wang; P. K. Datta; Q. Zhang; R. E. Gawley; R. M. Leblanc Langmuir, 2000, 16, 4607-4612.
"The Steric Course of SE2 Reactions of Unstabilized a-Aminoorganolithiums: Distinguishing Between SET and Polar Mechanisms" R. E. Gawley; E. Low; Q. Zhang; R. Harris J. Am. Chem. Soc. 2000, 122, 3344-3350.
"2-Lithio-N-BOC-thiazolidines as Chiral Acyl Anion Synthons: Evaluation of Facial Selectivity in the Addition of Chiral Organolithiums to Aldehydes" R. E. Gawley; Q. Zhang; A. T. McPhail, Tetrahedron: Asymmetry 2000, 11, 2093-2106.
"Synthesis and Reactivity of Conformationally Locked a-Aminoorganostannanes and a-Aminoorganolithiums. Discovery of a Surprising Configurational Requirement for Transmetalation" G. Chambournier; R. E. Gawley Org. Lett. 2000, 2, 1561-1564.
"Synthesis and Reactivity of Dipole-Stabilized but Unchelated a-Aminoorganolithiums" D. Iula and R. E. Gawley J. Org. Chem. 2000, 65, 6196-6201.
"Solution Structure of Unstabilized Cyclic a-Aminoorganolithiums by 13C, 15N, and 6Li NMR Spectroscopy" E. Low and R. E. Gawley J. Am. Chem. Soc. 2000, 122, 9562-9563.
"Computational, ReactIR-, and NMR-Spectroscopic Investigations on the Chiral Formyl Anion Equivalent N-(a-Lithiomethylthiomethyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one and Related Compounds" C. Gaul; P. I. Arvidsson; W. Bauer; R. E. Gawley; D. Seebach Chem. Eur. J. 2001, 7, 4117-4125.
"An Improved Synthesis of a Trifurcated Newkome-Type Monomer and an Orthogonally Protected 2-Generation Dendron" C. M. Cardona and R. E. Gawley, J. Org. Chem. 2002, 67, 1411-1413.
"Lithiated Camphor-Derived Oxazolidinone S,N-Acetals as Chiral Formyl Anion Synthons in Additions to Aldehydes. Asymmetric Synthesis of a-Hydroxy Aldehydes and a-Hydroxy Acids" R. E. Gawley, S. A. Campagna, M. Santiago, and T. Ren, Tetrahedron: Asymmetry 2002, 13, 29-36.
“Chemosensors for the Marine Toxin Saxitoxin” R. E. Gawley, S. Pinet; C. M. Cardona; P. K. Datta; T. Ren; W. C. Guida; J. Nydick; R. M. Leblanc, J. Am. Chem. Soc. 2002, 124, 13448-13453. This paper was featured in the web magazine ‘The Alchemist’ (http://www.chemweb.com/alchem/articles/1035208189509.html), in Nature (http://www.nature.com/nsu/021111/021111-4.html), and Trends in Analytical Chemistry (2003, 22(1), iv).
“Are Pfiesteria Species Toxicogenic? Evidence Against Production of Polyketides, Non-ribosomal Peptides, or any Ichthyotoxins by Pfiesteria shumwayae” J. P. Berry; K. S. Reece; K. S. Rein; D. G. Baden; L. W. Haas; W. Ribeiro; J. D. Shields; W. K. Vogelbein; R. E. Gawley, Proc. Nat. Acad. Sci. 2002, 99, 10970-10975. This paper was featured in or on CNN, Associated Press, Reuters, Science, New Scientist, Science News, C&ENews, the New York Times.
“A Theoretical Investigation into the Inversion Barrier of Dipole-Stabilized ?-Amino¬organolithiums” F. Hæffner; P. Brandt; R. E. Gawley Org. Lett. 2002, 4, 2101-2104.
“Coumaryl crown ether based chemosensors for saxitoxin in water. Selective detection in the presence of sodium and potassium ions”, P. Kele; J. Orbulescu; T. L. Calhoun; R. E. Gawley; R. M. Leblanc Tetrahedron Lett. 2002, 43, 4413-4416.
“Langmuir Monolayer and Langmuir-Blodgett Film Studies of an Amphiphilic Coumaryl Crown Ether”, P. Kele; J. Orbulescu, T. L. Calhoun, R. E. Gawley, R. M. Leblanc, Langmuir 2002, 18, 8523-8526.
“Spatially Resolved Derivatization of Solid-Phase Synthesis Beads with Fluorescent Dendrimers. Creation of Localized Microdomains”, Claudia M. Cardona, Stephan H. Jannach, Hao Huang, Yukiko Itojima, Roger M. Leblanc, Gary A. Baker, Eric B. Brauns, and Robert E. Gawley, Helv. Chim. Acta, 2002, 85, 3532-3558.
“?-Aminoorganolithiums”, R. E. Gawley and I. Coldham, in The Chemistry of Organolithium Compounds, Z. Rappoport and I. Marek, Eds, Wiley, 2004, 997-1053.
“Isolation of Bioactive Metabolites from a Lyngbya Species Isolated from Periphyton of the Florida Everglades”, J. P. Berry, M. Gantar, R. E. Gawley, and K. S. Rein, In Harmful Algae 2002: Proceedings of the Xth International Conference on Harmful Algal Blooms, K. A. Steidinger, J. H. Landsberg, C. Tomas, G. A. Vargo, eds. 2004, Florida Fish and Wildlife Conservation Commission, Florida Institute of Oceanography, and Intergovernmental Oceanographic Commission of UNESCO, St. Petersburg, Florida, USA, pp. 192-194.
“Modeling and Experiment Reveal an Unexpected Stereoelectronic Effect on Conformation and Scalar Couplings of ?-Aminoorganostannanes, with Possible Relevance to the Tin-Lithium Exchange Reaction” M. Santiago, E. Low, G. Chambournier, R. E. Gawley, J. Org. Chem. 2003, 68, 8480-8484.
“Microwave Assisted Solvent Free Amination of Halo-(Pyridine or Pyrimidine) without Transition Metal Catalyst” S. Narayan, T. Seelhammer and R. E. Gawley Tetrahedron Lett., 2004, 45, 757-759.
“Nucleophilic Synthesis of Enantiopure 2-(Tributylstannyl)pyrrolidines and Piperidines” R. E. Gawley, G. Barolli, S. Madan, M. Saverin, and S. O'Connor Tetrahedron Lett. 2004, 45, 1759-1761.
“Pharmacology and Toxicology of Pahayokolide A, a Bioactive Metabolite from a Freshwater Species of Lyngbya Isolated from the Florida Everglades” J. P. Berry, M. Gantar, R. E. Gawley, M. Wang, K. S. Rein Compar. Biochem. Physiol. C 2004, 139, 231-238.
“Chirality Made Simple: a 1- and 2-Dimensional Introduction to Stereochemistry” R. E. Gawley J. Chem. Educ., 2005, 1009-1012.
“The Barrier to Enantiomerization of Unstabilized, Chelated, and Dipole-Stabilized 2-Lithiopyrrolidines” N. J. Ashweek, P. Brandt, I. Coldham, S. Dufour, R. E. Gawley, F. Haeffner, R. Klein, G. Sanchez-Jimenez J. Amer. Chem. Soc. 2005, 127, 449-457.
“Absolute Configuration of 2-(tributylstannyl)-pyrrolidine by Anomalous Dispersion X-ray Analysis” R. E. Gawley, S. Narayan, D. A. Vicic J. Org. Chem. 2005, 70, 328-329.
“Conversion of 5-, 6-, and 7-Membered Lactams to Racemic or Scalemic 2-Substituted Heterocycles by Amidoalkylation” S. Madan, P. Milano, D. B. Eddings, R. E. Gawley J. Org. Chem. 2005, 70, 3066-3071.
“Structural Studies of {6Li} 2-Lithiopyrrolidines Using NMR Spectroscopy” R. E. Gawley, R. Klein, N. Ashweek, I. Coldham Tetrahedron 2005, 61, 3271-3280.
“Selective Detection of Saxitoxin over Tetrodotoxin Using Acridinylmethyl Crown Ether Chemosensor” Robert E. Gawley, Muthian Shanmugasundaram, John B. Thorne, and Richard M. Tarkka Toxicon, 2005, 45, 783-787; corrigendum 2005, 46, 477.
“Heptapeptide Mimic of the Ohmefentanyl Binding Site in the Discontinuous ?-Opiod Receptor” Robert E. Gawley, Mykhalo Dukh, Claudia M. Cardona, Stephan H. Jannach, Denise Greathouse Org. Lett. 2005, 7, 2953-2956.
“Stannylcyclopropanes by Diastereoselective Cyclopropanations with (Tributylstannyl)-Diazoacetate Esters Catalyzed by Cu(I) N-Heterocyclic Carbene” R. E. Gawley and S. Narayan Chem. Commun. 2005, 5109-5111.
“Product Subclass 21: ?-Lithioamines”, R. E. Gawley, S. O’Connor, and R. Klein, in Science of Synthesis (Houben-Weyl), vol. 8a, chapter 8.1.21, V. Snieckus and M. Majewski, Eds., Thieme: Stuttgart, 2006, pp 677-757.
“Do the Terms “%ee” and “%de” Make Sense as Expressions of Stereoisomer Composition or Stereoselectivity?” R. E. Gawley, J. Org. Chem., 2006, 71, 2411-2416.
"Spectroscopic detection of Saxitoxin: An alternative to mouse bioassay" P. Kele, J. Orbulescu, R. E. Gawley, R. M. Leblanc Chem. Commun. 2006, 1494-1496.
"Effect of Crown Ether Ring Size on Binding and Fluorescence Response to Saxitoxin in Anthracylmethyl Monoaza Crown Ether Chemosensors" Hua Mao, John B. Thorne, Jennifer S. Pharr and Robert E. Gawley, Can. J. Chem., 2006, 84, 1273-1279.
"Diastereoselectivity of Polar and Radical Couplings in Electrophilic Substitutions of Rigid 2-Lithio-N-methylpyrrolidines" R. E. Gawley, D. B. Eddings, M. Santiago, Org. Biomol. Chem. 2006, 4, 4285-4291
"Visible Fluorescence Chemosensor for Saxitoxin" Robert E. Gawley, Hua Mao, M. Mahbubul Haque, John B. Thorne, and Jennifer S. Pharr, J. Org. Chem. 2007, 72, 2187-2191.
"Configurational and Conformational Effects on Tin-Lithium Exchange in ±-Aminoorganostannanes by Rapid-Injection NMR", R. Klein and R. E. Gawley, J. Am. Chem. Soc. 2007, 129, 4126.
"Structures of Pahayokolides A and B, Two Cyclic Peptides from a Lyngbya sp." T. An, T. K. S. Kumar, M. Wang, L. Lu, J. O. Lay, Jr., R. Liyanage, J. Berry, M. Gantar, V. Marks, R. E. Gawley, and K. S. Rein, J. Nat. Prod., 2007, 70, 730-735.
"Stereoselective [2,3]-Sigmatropic Rearrangements of Unstabilized Nitrogen Ylides" R. E. Gawley and K. Moon Org. Lett. 2007, 9, 3093-3096.
"The barrier to enantiomerization of N-Boc-2-lithopyrrolidine: the effect of chiral and achiral diamines" Taher I. Yousaf, Roger L. Williams, Iain Coldham, and Robert E. Gawley Chem. Commun. 2008, 97-98.
"Dynamics of Saxitoxin Binding to Saxiphilin C-lobe Reveals Conformational Change" P. Lewis, I., R. E. Gawley, R. Henry, A. Kight, J. O. Lay, Jr., R. Liyanage, J. McLachlin Toxicon 2008, 51, 208-217.