Home / People / / Jon Antilla

Jon Antilla——Professor

Nationality:
USA
Phone:
+86 186 9805 5848
Email:
jantilla@tju.edu.cn
Office:
Room B610, Building 24, Tianjin University
School:
School of Pharmaceutical Science and Technology
ResearcherID:
Group weblink
Education Experience
2000 Ph. D. University of Chicago
1995 M.S. Northern Michigan University
Professional Experience
2003-2005 Associate Professor The University of Mississippi
2005-2015 Associate professor The University of South Florida
2015- Professor The University of South Florida
2016- Professor Tianjin university
Research Area

Our group’s focus has been mainly in the development of new catalytic methodology for organic synthesis. Our group is a recognized leader in the area of asymmetric organocatalysis with chiral phosphoric acids. Our methodology in the formation of aminals, in the reduction of imines, desymmetrization of meso-aziridines, and pinnacol rearrangement, for example, have been highly cited extensively (3,679 citations and H-index of 26). Our methods have used in the synthesis of biologically important targets by others, for example: Benjamin List (JACS, 2008, 15786) and Scott Snyder (Angew. Chem. Int. Ed., 2012, 51, 4080. Our aim has been to develop catalytic variants of existing, important reactions, to offer stereochemical control (regioselective, diastereoselective, or enantioselective) and higher efficiency, thus lower the potential costs to make drug targets. As a result we have been considered one of the leading groups in organocatalysis, especially in chiral phosphoric acid based catalysis. Our work has been recognized with a USA National Science Foundation CAREER award, a Thieme Journal Award, and also I was awarded with a JSPS Fellowship to Japan, a great honor. Additionally, part of our work has been to seek “green” alternatives to existing methods, as the use of organocatalysis avoids the employment of potentially toxic metals in an environmentally benign manner.

Honors and Awards
External Funding (Active, Ongoing Support) 1. “Chiral Phosphoric Acid-Catalyzed Reaction Methodology and Synthetic Applications” Agency: NSF 4/1/09-9/1/14 $550,000 Type: CAREER Award, single investigator
External Funding (Previous Support) 1. “Synthesis and Screening of Sigma Ligands for Stroke Treatment at Delayed Time Points” Agency: James and Ester King Biomedical Research 7/1/09-6/30/11 $999,360 Type: Florida Department of Health State Grant (Co-PI on this Team Science Grant)
Agency: Petroleum Research Fund 1/1/07-8/31/09 $40,000 Type: Type G Starter Grant, single investigator
3. “The development of New Stereoselective Organocatalytic Processes” Agency: NIH 9/1/08-8/31/13 $1,318,849 Type: R01, single investigator
Patents
Brønsted Acid-Catalyzed Asymmetric Allylation of Aldehydes, Antilla, J. C.; Jain, P., 13 May 2010. Patent Application, USF Ref. No. 10A057.
N,N’-di-p-bromophenyl Guanidine Treatment for Stroke at Delayed Timepoints, Pennypacker, K.; Cuevas, J.; Antilla, J. C.; Cortes-Salva, M., 12 Nov 2008. Patent Application, USF Ref. No. 08A048PR.
Enantio-Selective Brønsted Acid-Catalyzed Ring-Opening of Azirdines, Antilla, J. C.; Rowland, E. B.; Rowland G. B., 29 June 2007. Patent Application, USF Ref. No. 07A029PR.
Process for Producing Optically Active β-Amino Esters Using Metal-Chiral Ligand Catalytic Compounds, Wulff, W. D.; Antilla, J. C.; Yu, S., Provisional Patent Application # 104147
Copper-Catalyzed Formation of Carbon-Heteroatom and Carbon-Carbon Bonds, Buchwald, S. L.; Klapars, A.; Antilla, J. C.; Job, G. E.; Wolter, M.; Kwong, F. Y.; Nordmann, G.; Hennessy, E. J., United States Patent, 15 March 2005. Patent No.: 6,867,298.
Copper-Catalyzed Formation of Carbon-Heteroatom and Carbon-Carbon Bonds, Buchwald, S. L.; Klapars, A.; Antilla, J. C.; Job, G. E.; Wolter, M.; Kwong, F. Y.; Nordmann, G.; Hennessy, E. J., United States Patent, 6 July 2004. Patent No.: 6,759,554.
Process for the Catalytic Asymmetric Synthesis of Chiral Aziridines, Wulff, W. D.; Antilla, J. C., United States Patent, 10 July 2001. Patent No.: 6,258,960.
Highlighted Publications
“Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction,” He, Y.; Lin, M.; Li, Z.; Liang, X.; Li, G.; Antilla, J. C., Org. Lett. 2011, 13, 4490.
“Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (-)- Debromoflustramine B,” Zhang, Z.; Antilla, J. C., Angew. Chem. Int. Ed. 2012, 51, 11778.
“Origins of Stereoselectivities in Chiral Phosphoric Acid Catalyzed Allylborations and Propargylations of Aldehydes,” Wang, H.; Jain, P.,; Antilla, J. C.; Houk, K. N. The Journal of Organic Chemistry 2013, 78, 1208.
“An Asymmetric Diels-Alder Reaction Catalyzed by Chiral Phosphate Magnesium Complexes: Highly Enantioselective Synthesis of Chiral Spirooxindoles,” Li, G.; Liang, T.; Wojtas, L.; Antilla, J. C., Angew. Chem. Int. Ed. 2013, 52, 4628.
“Palladium-Catalyzed Tunable Functionalization of Allylic Imidates: Regioselective Aminoacetoxylation and Aziridination,” Cui, S.; Wojtas, L.; Antilla, J. C. Angew. Chem. Int. Ed. 2011, 50, 8927.
"Catalytic Asymmetric Aziridination with a Chiral VAPOL-Boron Lewis Acid," Antilla, J. C.; Wulff, W. D., J. Am. Chem. Soc. 1999, 121, 5099-5100.
"Catalytic Asymmetric Aziridination with Aryl Borate Catalysts Derived from VAPOL and VANOL Ligands," Antilla, J. C.; Wulff, W. D., Angew. Chem. Int. Ed., 2000, 39, 4518-4521.
"Copper-Catalyzed Coupling of Arylboronic Acids and Amines," Antilla, J. C.; Buchwald, S. L. Org. Lett., 2001, 3, 2077-2079.
"A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles," Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
“Copper-Catalyzed N-Arylation of Indoles,” Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684-11688.
“Copper-Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles,” Antilla, J. C.; Baskin, J.; Barder, T.; Buchwald, S. L., J. Org. Chem. 2004, 69, 5578.
“Brønsted Acid-Catalyzed Imine Amidation,” Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang Y.; Antilla, J. C., J. Am. Chem. Soc. 2005, 127, 15696.
“Stereoselective Aza-Diels-Alder Reactions,” Rowland, G. B.; Rowland, G. B.; Zhang Q.; Antilla, J. C., Current Organic Chemistry, 2006, 10, 981.
"A Vaulted Biaryl Phosphoric Acid-Catalyzed Reduction of α-Imino Esters: The Highly Enantioselective Preparation of α-Amino Esters," Li, G.; Liang, Y.; Antilla, J. C., J. Am. Chem. Soc. 2007, 129, 5830.
“Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines,” Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C., J. Am. Chem. Soc. 2007, 129, 12084.
“Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective Preparation of Chiral N,O-Aminals,” Li, G.; Fronczek, F. R.; Antilla, J. C., J. Am. Chem. Soc. 2008, 130, 12216.
“Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans,” Larson, S.; Baso, J.; Li, G.; Antilla, J. C., Org. Lett. 2009, 11, 5186.
“Chiral Brønsted Acid-Catalyzed Pinacol Rearrangement,” Liang, T.; Zhang, Z.; Antilla, J. C., Angew. Chem. Int. Ed. 2010, 49, 9734.
“Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals,” Ingle, G. K.; Mormino M. G.; Li G.; Wojtas, L.; Antilla, J. C., Org. Lett. 2011, 13, 4822.
“Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts,” Zhang, Z.; Jain, P.; Antilla, J. C., Angew. Chem. Int. Ed. 2011, 50, 10961.
“In vitro evaluation of guanidine analogues as sigma receptor ligands for potential anti-stroke therapeutics,” Behansky, A. A.; Cortes-Salva, M.; Seminerio, M. J.; Matsumoto, R. R.; Antilla, J. C.; Cuevas, J. J. Pharmacol.Exp. Ther. 2012, 344(1), 155.
“In Vitro Evaluation of Guanidine Analogs as Sigma Receptor Ligands for Potential Anti-Stroke Therapeutics,” Behensky, A. A.; Cortes-Salva, M.; Seminerio, M. J.; Matsumoto, R. R.; Antilla, J. C.; Cuevas, J. J. Pharm. Exp. Ther. 2013, 344, 155.
“Two Homochiral Organocatalytic Metal Organic Materials with Nanoscopic Channels,” Zhang, Z.; Ji, Y. R; Wojtas, L.; Gao, W-. Y.; Ma, S.; Zaworotko, M. J.; Antilla, J. C., Chem. Commun. 2013, 49, 7693.
“Novel Nicotinic Receptor Agonists Improve Gait and Balance in Olivocerebellar Ataxia,” Wecker, L.; Enberg, M.E.; Philpot, R. M.; Lambert, C. S.; Kang, C. W.; Antilla, J. C.; Bickford, P. C.; Hudson, C. E.; Zesiewicz, C. A. Neuropharmacology 2013, 73, 75.
“Asymmetric One-Pot Synthesis of 1,3-Oxazolidines and 1,3-Oxazinanes via Hemiaminal Intermediates,” Nimmagadda, S. K.; Zhang, Z.; Antilla, J. C., Org. Lett. 2014, 16, 4098.
“Chiral metal phosphate catalysis: highly asymmetric hetero-Diels-Alder reactions,” Liang, T.; Li, G.; Wojtas, L.; Antilla, J. C., Chem. Commun. 2014, 50, 14187.
ResearcherID Publications
Year Title Author(s) Source Volume