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Jon Antilla

Jon Antilla

Jon Antilla
Associate Professor

Contact

Office: NES 230
Lab: NES 332
Phone: 813/974-7438
Email:

Links

Education

B.S., Northern Michigan University, 1995
Ph.D., University of Chicago, 2000
Postdoctoral Fellow (NIH-NCI), Massachusetts Institute of Technology, 2000-2003

Research

Chiral Organocatalysis, Metal-Catalysis, New Stereoselective Reaction Methodology, Drug Discovery.

We have now made significant inroads into a new area of organocatalysis that utilize chiral Phosphoric acids in a number of interesting synthetic transformations. We have published the first examples in the literature where chiral N,N- or N,O-aminals can be formed in a catalytic enantioselective manner. This new approach to catalysis should allow for the general synthesis of highly desired chiral heterocycles. Recently, we have begun collaboration with the medical center to develop drugs for post-stroke treatment. These potential drugs are based upon a promising lead structure with a guanidine core. We are currently developing synthetic routes to synthetic guanidine analogues.

Current Funding

View our currently funded projects here.

Ongoing Research Support

Title: The development of New Stereoselective Organocatalytic Processes (Sole PI)
Agency: NIH - $ 1,318,849.00 - 9/1/08-8/31/13
Type: R01 (GM082935) (Sole PI)

Title: Chiral Phosphoric Acid-Catalyzed Reaction Methodology and Synthetic Applications
Agency: NSF - $ 550,000 - 4/1/09-3/31/14
Type: CAREER (CHE-0847108) (Sole PI)

Title: Synthesis and Screening of Sigma Ligands for Stroke Treatment at Delayed Time Points
Agency: James and Ester King Biomedical Research - $ 999,360 - 7/1/09-6/30/11
Type: Florida Department of Health State Grant (Co-PI on this Team Science Grant)

Completed Research Support

Title: Synthesis and Screening of Sigma Receptor Ligands for Stroke Therapy at Delayed Time Points
Agency: FCoE-BITT (Co-PI on this seed grant) - $ 75,000 - 2/1/08-1/31/09
Type: Internal Grant

Title: Brønsted Acid-Catalyzed Asymmetric Additions to Imines (Sole PI)
Agency: PRF - $ 40,000.00 - 1/1/07-8/31/09
Type: Type G Starter (PRF# 45899-G1) (Sole PI)

Title: Novel Neuronal Nicotinic Receptor Modulators for the Treatment of Ataxia
Agency: FCoE-BITT - $ 70,000 - 5/1/09-4/30/10
Type: Internal Grant (Co-PI on this seed grant)

Group Photo

Antilla Group

Visting Professor

Dr. Sebastien Comesse

Postdoctoral Associates and Visiting Scholars

Dr. Zuhui Zhang, Dr. Wenhua Zheng, Dr. Sunliang Cui, Dr. Alice Beauseigneur

Graduate Students

Pankaj Jain, Young Ran Ji, Matthew Kaplan, Tao Liang, Susana Lopez, Yi Si

Recent Publications

Publications from Doctoral Studies:

  1. Antilla, J. C.; Wulff, W. D. "Catalytic Asymmetric Aziridination with a Chiral VAPOL-Boron Lewis Acid," J. Am. Chem. Soc. 1999, 121, 5099-5100.
  2. Antilla, J. C.; Wulff, W. D. "Catalytic Asymmetric Aziridination with Aryl Borate Catalysts Derived from VAPOL and VANOL Ligands," Angew. Chem. Int. Ed. 2000, 39, 4518-4521.
  3. Newman, C. A.; Antilla, J. C.; Chen, P.; Wulff, W. D., "Regulation of Orthogonal Functions in a Dual Catalyst System. Subservient Role of a Non-chiral Lewis Acid in an Asymmetric Catalytic Heteroatom Diels-Alder Reaction," J. Am. Chem. Soc. 2007, 129, 7216.

Publications from Postdoctoral Work:

  1. Antilla, J. C.; Buchwald, S. L. "Copper-Catalyzed Coupling of Arylboronic Acids and Amines," Org. Lett. 2001, 3, 2077-2079.
  2. Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. "A General and Efficient Copper Catalyst for the Amidation of Aryl Halides and the N-Arylation of Nitrogen Heterocycles," J. Am. Chem. Soc. 2001, 123, 7727-7729.
  3. Antilla, J. C.; Klapars, A.; Buchwald, S. L. "Copper-Catalyzed N-Arylation of Indoles," J. Am. Chem. Soc. 2002, 124, 11684-11688.
  4. Antilla, J. C.; Baskin, J. M.; Barder T. E.; Buchwald, S. L. "Copper-Diamine-Catalyzed N-Arylation of Pyrroles, Pyrazoles, Indazoles, Imidazoles, and Triazoles," J. Org. Chem. 2004, 69, 5578-5587.

Publications as an Independent Investigator:

  1. Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. "Brønsted Acid-Catalyzed Imine Amidation," J. Am. Chem. Soc. 2005, 127, 15696-15697.
  2. Rowland, G. B.; Rowland, E. B.; Zhang, Q.; Antilla, J. C. "Stereoselective Aza-Diels-Alder Reactions," Current Organic Chemistry, 2006, 10, 981-1005.
  3. Li, G.; Liang, Y.; Antilla, J. C., "A Vaulted Biaryl Phosphoric Acid-Catalyzed Reduction of a-Imino Esters: The Highly Enantioselective Preparation of a-Amino Esters," J. Am. Chem. Soc. 2007, 129, 5830.
  4. Rowland, G. B.; Rowland, E. B.; Liang, Y.; Perman, J. A.; Antilla, J. C., "The Highly Enantioselective Addition of Indoles to N-Acyl Imines with Use of a Chiral Phosphoric Acid Catalyst," Org. Lett. 2007, 9, 2609.
  5. Li, G.; Rowland, G. B.; Rowland, E. B.; Antilla, J. C., "Organocatalytic Enantioselective Friedel-Crafts Reaction of Pyrrole Derivatives with Imines," Org. Lett. 2007, 9, 4065.
  6. Liang, Y.; Rowland, E. B.; Rowland, G. B.; Perman, J. A.; Antilla, J. C., "VAPOL phosphoric acid catalysis: the highly enantioselective addition of imides to imines," Chem. Commun. 2007, 43, 4477.
  7. Rowland, E. B.; Rowland, G. B.; Rivera-Otero, E.; Antilla, J. C., "Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines," J. Am. Chem. Soc. 2007, 129, 12084.
  8. Li, G.; Fronczek, F. R.; Antilla, J. C., "Catalytic Asymmetric Addition of Alcohols to Imines: Enantioselective Preparation of Chiral N,O-Aminals," J. Am. Chem. Soc. 2008, 130, 12216.
  9. Li, G.; Antilla, J. C., "Highly Enantioselective Hydrogenation of Enamides Catalyzed by Chiral Phosphoric Acids," Org. Lett. 2009, 11, 1075.
  10. Larson, S.; Baso, J.; Li, G.; Antilla, J. C., "Chiral Phosphoric Acid-Catalyzed Desymmetrization of meso-Aziridines with Functionalized Mercaptans," Org. Lett. 2009, 11, 5186.
  11. Cortes-Salva, M.; Nguyen, L.; Cuevas, J.; Pennypacker, K.; Antilla, J. C., "Copper-Catalyzed Guanidine Arylation," Org. Lett. 2010, 12, 1316.
  12. Li, G.; Kaplan, M. J.; Wojtas, L.; Antilla, J. C., "Chiral Phosphoric Acid-Catalyzed Addition of Dihydropyrans to N-Acyl Imines: Stereocontrolled Access to Enantioenriched Spirocyclic Oxazoletetrahydropyrans with Three Contiguous Stereocenters," Org. Lett. 2010, 12, 1960.
  13. Desai, A. A.; Huang, L.; Wulff, W. D.; Rowland, G. B.; Antilla, J. C., "Gram-Scale Preparation of VAPOL Hydrogenphosphate: A Structurally Distinct Chiral Brønsted Acid," Synthesis. 2010, 12, 2106.
  14. Zheng, W.; Wojtas, L.; Antilla, J. C., "Chiral Phosphoric Acid-Catalyzed Peroxidation of Imines," Angewandte Chemie, Early View, 2010.
  15. Jain, P.; Antilla, J. C., "Chiral Brønsted Acid-Catalyzed Allylboration of Aldehydes," J. Am. Chem. Soc., ASAP, 2010.
  16. Liang, Y.; Ingle, G.; Li, G.; Fronczek, F. R.; Antilla, J. C., "Chiral Phosphoric Acid-Catalyzed Phosphination of Imines: Access to Enantioenriched a-Amino Phosphines," In Revision for Organic Letters.
  17. Li, G.; Rowland, G. B.; Huang, R.; Junge, D. M.; Antilla, J. C., "A Chiral Phosphoric Acid-Catalyzed Aza-Darzens Route to Aziridines," Preparing to be Submitted to Organic Letters.

Patents and Patent Applications:

  1. 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.
  2. 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.
  3. 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.
  4. Process for Producing Optically Active ß-Amino Esters Using Metal-Chiral Ligand Catalytic Compounds, Wulff, W. D.; Antilla, J. C.; Yu, S., Provisional Patent Application # 104147.
  5. 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.
  6. Brønsted Acid-Catalyzed Asymmetric Allylation of Aldehydes, Antilla, J. C.; Jain, P., 13 May 2010. Patent Application, USF Ref. No. 10A057.