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Faculty

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Alison J. Frontier

  • Professor of Chemistry

PhD, Columbia University, 1999

414 Hutchison Hall
(585) 275-2568
frontier@chem.rochester.edu

Website


Research Overview

The Frontier laboratory is engaged in synthetic organic chemistry research, especially cyclization reactions that produce unusual, densely functionalized ring systems from simple precursors. Research directions being pursued in the lab include the study of novel pericyclic reactions, cationic rearrangements and diastereoselective cyclization cascades, and their application to complex molecule synthesis.

Selected Publications

  • Huang, Yu-Wen, Frontier, Alison J. “Nazarov Cyclization/Internal Redox Cyclization Sequence for the Synthesis of N-Heterocyclic Bridged Ring Systems” Org. Lett. 201618, 4896-4899. doi: 10.1021/acs.orglett.6b02369
  • Huang, Yu-Wen; Frontier, Alison J. “Enantioselective Nazarov cyclization catalyzed by a Cinchona alkaloid derivative.” Invited paper for special issue honoring Harry Wasserman, Tetrahedron Lett. 201556, 3523-3526.
  • Jacob, Steven; Brooks, Joshua L.; Frontier, Alison J. “No Acid Required: 4pi and 6pi Electrocyclization Reactions of Dienyl Diketones for the Synthesis of Cyclopentenones and 2H-Pyrans”. J. Org. Chem. 2014, 79, 10296–10302.
  • Carlsen, P.N., Mann, T.J., Hoveyda, A.H., Frontier, A. J. "Synthesis of (±)-Tetrapetalone A-Me Aglycon," Angew Chem. Int. Ed.2014, DOI: http://dx.doi.org/10.1002/anie.201404410.
  • Vaidya, T., Cheng, R., Carlsen, P.N., Frontier, A. J., Eisenberg, R. "Cationic Cyclizations and Rearrangements Promoted by a Heterogeneous Gold Catalyst," Org. Lett.2014, 16, 800-803.
  • Ciesielski, J., Gandon, V., Frontier, A. J. "Cascade of Acyclic and Macrocyclic Alkynones: Studies toward the Synthesis of Phomactin A.," J. Org. Chem.2013, 78, 9541-9552.
  • Spencer, W.T. II, Vaidya, T., Frontier, A. J. "Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates," Eur. J. Org. Chem.2013, 3621-3633 (Microreview).
  • Leboeuf, D., Huang, J., Gandon, V., Frontier, A. J.  "Using Nazarov Electrocyclization to Stage Chemoselective [1,2]-Migrations: Stereoselective Synthesis of Functionalized Cyclopentenones,"  Angewandte Chem. Int. Ed.  2011,  50,  10981-10985.
  • Vaidya, T., Eisenberg, R., Frontier, A. J.  "Catalytic Nazarov Cyclization: The State of the Art,"  Chem. Cat. Chem.  2011,  3,  1531-1548.
  • Brooks, J. L., Caruana, P. A., Frontier, A. J.  "Conjugate Addition-Initiated Nazarov Cyclization,"  J. Am. Chem. Soc.  2011,  133,  12454-12457.
  • Huang, J., Leboeuf, D., Frontier, A. J.  "Understanding the Fate of the Oxyallyl Cation following Nazarov Electrocyclization: Sequential Wagner-Meerwwin Migrations and the Synthesis of Spirocyclic Cyclopentenones,"  J. Am. Chem. Soc.  2011,  133,  6307-6317.
  • Vaidya, T., Manbeck, G. R., Chen, S., Frontier, A. J.  "Divergent Reaction Pathways of a Cationic Intermediate: Rearrangement and Cyclization of 2-Substituted Furyl and Benzofuryl Enones Catalyzed by Iridium(III),"  J. Am. Chem. Soc.  2011,  133,  3300-3303.
  • Ciesielski, J., Canterbury, D. P., Frontier, A. J.  "β-Iodoallenolates as Springboards for Annulation Reactions,"  Org. Lett.  2009,  11,  4374-4377.
  • Malona, J. M., Cariou, K., Frontier, A. J.  "Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (±)-Rocaglamide,"  J. Am. Chem. Soc.  2009,  131, 7560-7561.
  • He, W., Herrick, I. R., Atesin, T. A., Caruana, P. A., Kellenberger, C. A., Frontier, A. J.  "Polarizing the Nazarov Cyclization: The Impact of Dienone Substitution Pattern on Reactivity and Selectivity,"  J. Am. Chem. Soc.  2008,  130,  1003-1011.
  • He, W., Huang, J., Frontier, A. J.  "Total Synthesis of (±)-Merrilactone A,"  J. Am. Chem. Soc.  2008,  130,  300-308.
  • Huang, J., Frontier, A. J.  "Development of a Nazarov Cyclization/ Wagner-Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles,"  J. Am. Chem. Soc.  2007,  129,  8060-8061.