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Jon  Antilla

Jon Antilla

Jon Antilla
Associate Professor

Contact

Office: NES 230
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 now made significant inroads into a new area of organocatalysis that utilize chiral phosphoric acids and chiral metal phosphate complexes 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 has allowed for the general synthesis of highly desired chiral heterocycles. We have also collaborated 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 have developed 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)

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)

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)

Postdoctoral Associates and Visiting Scholars

Dr. Zhongang Mu, Dr. Guilong Li, Dr. Zuhui Zhang

Graduate Students

Pankaj Jain, Young Ran Ji, Tao Liang, Susana Lopez, Sri Krishna Nimmagadda, Demetrios Pantages

Current Courses

RefCourseSecCourse TitleCRDayTimeLocation
13280CHM 2211901Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
8:00am-8:50am
3:30pm-5:00pm
6:30pm-7:45pm
NES 108
EXAM F100
BSF 100
13281CHM 2211902Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
9:05am-9:55am
3:30pm-5:00pm
6:30pm-7:45pm
ISA 3050
EXAM F100
BSF 100
13282CHM 2211903Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
10:10am-11:00am
3:30pm-5:00pm
6:30pm-7:45pm
CMC 13
EXAM F100
BSF 100
13794CHM 2211904Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
11:15am-12:05pm
3:30pm-5:00pm
6:30pm-7:45pm
ISA 3050
EXAM F100
BSF 100
13795CHM 2211905Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
12:20pm-1:10pm
3:30pm-5:00pm
6:30pm-7:45pm
CMC 13
EXAM F100
BSF 100
13796CHM 2211906Organic Chemistry II
F, 3:30pm-5:00pm is your scheduled exam time. You can register in organic chem II lecture w/out the lab,
3F
F
TR
1:25pm-2:15pm
3:30pm-5:00pm
6:30pm-7:45pm
EDU 313
EXAM F100
BSF 100
13483CHM 4970002Undergraduate Research
Requires Instructor Approval S-U Only
1-3
TBA TBA
13569CHM 6971002Thesis: Master's
S-U Only
2-19
TBA TBA
10151CHM 6973002Directed Research
S-U Only
1
TBA TBA
13528CHM 7820002Directed Research
S-U Only
1-19
TBA TBA
13549CHM 7980002Dissertation: Doctoral
Adm To Doc Candidacy Req S-U Only
2-19
TBA TBA

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. Cortes-Salva, M.; Nguyen, L.; Cuevas, J.; Pennypacker, K.; Antilla, J. C., "Copper-Catalyzed Guanidine Arylation," Org. Lett. 2010, 12, 1316.
  2. 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.
  3. 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.
  4. Zheng, W.; Wojtas, L.; Antilla, J. C., "Chiral Phosphoric Acid-Catalyzed Peroxidation of Imines," Angewandte Chemie, Early View, 2010.
  5. Jain, P.; Antilla, J. C., "Chiral Brønsted Acid-Catalyzed Allylboration of Aldehydes," J. Am. Chem. Soc., ASAP, 2010.
  6. Liang, T.; Zhang, Z.; Antilla, J. C., “Chiral Brønsted Acid-Catalyzed Pinacol Rearrangement,” Angew. Chem. Int. Ed. 2010, 49, 9734.
  7. Cortes-Salva, M.; Garvin, C.; Antilla, J. C., “Ligand-Free Copper-Catalyzed Arylation of Amidines,” The Journal of Organic Chemistry 2011, 76, 1456.
  8. Zhang, Z.; Zheng, W.; Antilla, J. C., “Highly Enantioselective Catalytic Benzoyloxylation of 3-Aryloxindoles Using Chiral VAPOL Calcium Phosphate,” Angew. Chem. Int. Ed. 2011, 50, 1135.
  9. Cui, S.; Wojtas, L.; Antilla, J. C., “Palladium-Catalyzed Tunable Functionalization of Allylic Imidates: Regioselective Aminoacetoxylation and Aziridination,”  Angew. Chem. Int. Ed. 2011, 50, 8927.
  10. Zheng, W.; Zhang, Z. Kaplan, M. J.; Antilla, J. C., “Calcium Catalyzed Asymmetric Chlorination of Oxindoles,” The Journal of the American Chemical Society 2011, 133, 3339.
  11. Liang, Y.; Ingle, G.; Li, G.; Fronczek, F. R.; Antilla, J. C., “Chiral Magnesium BINOL Phosphate-Catalyzed Phosphination of Imines: Access to Enantioenriched a-Amino Phosphine Oxides,” Organic Letters 2011, 13, 2054.
  12. Larson, S. E.; Li, G.; Rowland, G. B.; Junge, D.; Huang, R.; Woodcock, H. L.; Antilla, J. C., “Catalytic Asymmetric Aza-Darzens Reaction with a Vaulted Biphenanthrol Magnesium Phosphate Salt,” Organic Letters 2011, 13, 2188.
  13. He, Y.; Lin, M.; Li, Z.; Liang, X.; Li, G.; Antilla, J. C.,  “Direct Synthesis of Chiral 1,2,3,4-Tetrahydropyrrolo[1,2-a]pyrazines via a Catalytic Asymmetric Intramolecular Aza-Friedel–Crafts Reaction,” Org. Lett. 2011, 13, 4490.
  14. Ingle, G. K.; Mormino M. G.; Li G.; Wojtas, L.; Antilla, J. C.,  “Chiral Phosphoric Acid-Catalyzed Addition of Thiols to N-Acyl Imines: Access to Chiral N,S-Acetals,” Org. Lett. 2011, 13, 4822.
  15. Cui, S.; Wojtas, L.; Antilla, J. C.,  “Palladium-Catalyzed C4-Olefination of Oxazoles via C-H Bond Activation: Divergent Synthesis of Functionalized Amino Alcohol and Amino Acid Derivatives,” Org. Lett. 2011, 13, 5040.
  16. Zhang, Z.; Jain, P.; Antilla, J. C., “Asymmetric Reduction of Ketones by Phosphoric Acid Derived Catalysts,” Angew. Chem. Int. Ed. 2011, 50, 10961.
  17. Jain, P.; Wang, H.; Houk, K. N.; Antilla, J. C., “Brønsted Acid-Catalyzed Asymmetric Propargylation of Aldehydes,” Angew. Chem. Int. Ed. 2012, 51, 1391.
  18. Zhang, Z.; Antilla, J. C., “Enantioselective Construction of Pyrroloindolines Catalyzed by Chiral Phosphoric Acids: Total Synthesis of (-)-Debromoflustramine B,” Angew. Chem. Int. Ed. 2012, 51, 11778.
  19. Behansky, A. A.; Cortes-Salva, M.; Seminerio, M. J.; Matsumoto, R. R.; Antilla, J. C.; Cuevas, J. J. “In vitro evaluation of guanidine analogues as sigma receptor ligands for potential anti-stroke therapeutics,” Pharmacol.Exp. Ther. 2012, 344(1), 155.
  20. Wang, H.; Jain, P.,; Antilla, J. C.; Houk, K. N. “Origins of Stereoselectivities in Chiral Phosphoric Acid Catalyzed Allylborations and Propargylations of Aldehydes,” The Journal of Organic Chemistry 2013, 78, 1208.
  21. Li, G.; Liang, T.; Wojtas, L.; Antilla, J. C., “An Asymmetric Diels-Alder Reaction Catalyzed by Chiral Phosphate Magnesium Complexes: Highly Enantioselective Synthesis of Chiral Spirooxindoles,” Angew. Chem. Int. Ed. 2013, 52, 4628.
  22. Zhang, Z.; Ji, Y. R; Wojtas, L.; Gao, W-. Y.; Ma, S.; Zaworotko, M. J.; Antilla, J. C., “Two Homochiral Organocatalytic Metal Organic Materials with Nanoscopic Channels,” Chem. Commun. 2013, 49, 7693.
  23. Wecker, L.; Zesiewicz, T. A.; Antilla, J. C.; Bickford, P. C.; Enberg, M. E.; Hudson, C. E.; Kang, C. W.; Lambert, C. S.; Philpot, R.; Powell, P. P., “Neuronal nicotinic receptor agonists improve gait and balance in oliverocerebellar ataxia," Neuropharmacology 2013, 73, 75.

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.