Alison J. Frontier

Alison J. Frontier

Professor of Chemistry

Ph.D. 1999, Columbia University

Synthetic organic chemistry; synthesis of bioactive natural products; pericyclic reactions; asymmetric catalysis; cationic cascades

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

Carlsen, P.N., Mann, T.J., Hoveyda, A.H., Frontier, A. J.  "Synthesis of (±)-Tetrapetalone A-Me Aglycon,"  Angew Chem. Int. Ed.  2014DOI:
Vaidya, T., Cheng, R., Carlsen, P.N., Frontier, A. J., Eisenberg, R.  "Cationic Cyclizations and Rearrangements Promoted by a Heterogeneous Gold Catalyst,"  Org. Lett.  201416800-803.
Ciesielski, J., Gandon, V., Frontier, A. J.  "Cascade of Acyclic and Macrocyclic Alkynones: Studies toward the Synthesis of Phomactin A.,"  J. Org. Chem.  2013789541-9552.
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.  20133621-3633 (Microreview).
Brooks, J.L., Frontier, A. J.  "Cyclization Cascades Initiated by 1,6-Conjugate Addition,"  J. Am. Chem. Soc.  2013135119362.
Leboeuf, D., Ciesielski, J., Gandon, V., Frontier, A. J.  "Experimental and Theoretical Studies on the Nazarov Cyclization/Wagner-Meerwein Rearrangement Sequence,"  J. Am. Chem. Soc.  20121346296-6308.
Malona, J. M., Cariou, K., Spencer, W. T., Frontier, A. J.  "Total Synthesis of (±)-Rocaglamide via Oxidation-Initiated Nazarov Cyclization,"  J. Org. Chem.  2012771891-1908.
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.  20115010981-10985.
Vaidya, T., Eisenberg, R., Frontier, A. J.  "Catalytic Nazarov Cyclization: The State of the Art,"  Chem. Cat. Chem.  201131531-1548.
Brooks, J. L., Caruana, P. A., Frontier, A. J.  "Conjugate Addition-Initiated Nazarov Cyclization,"  J. Am. Chem. Soc.  201113312454-12457.
Trost, B. M., Frontier, A. J., Thiel, O. R., Yang, H., Dong, G.  "Total Synthesis of Bryostatins: The Development of Methodology for the Atom-Economic and Stereoselective Synthesis of the Ring C Subunit,"  Chem. Eur. J.  2011179762-9776.
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.  20111336307-6317.
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.  20111333300-3303.
Spencer, W. T., Levin, M. D., Frontier, A. J.  "Oxidation-Initiated Nazarov Cyclization of Vinyl Alkoxyallenes,"  Org. Lett.  201113414-417.
Zhang, J., Vaidya, T., Brennessel, W. W., Frontier, A. J., Eisenberg, R.  "Dicationic Palladium(II) Complexes as Active Lewis Acid Catalysts for Polarized Nazarov Cyclization,"  Organometalics  2010293341-3349.
Vaidya, T., Atesin, A. C., Herrick, I. R., Frontier, A. J., Eisenberg, R.  "A Highly Reactive Dicationic Iridium(III) Catalyst for the Polarized Nazarov Cyclization Reaction,"  Angewandte Chem. Int. Ed.  2010493363-3366.
Atesin, A. C., Zhang, J., Vaidya, T., Brennessel, W. W., Frontier, A. J., Eisenberg, R.  "Synthesis, Characterization, and Catalytic Properties of New Electrophilic Iridium(III) Complexes Containing the (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Ligand,"  Org. Lett.  2010494331-4342.
Ciesielski, J., Canterbury, D. P., Frontier, A. J.  "β-Iodoallenolates as Springboards for Annulation Reactions,"  Org. Lett.  2009114374-4377.
Canterbury, D. P., Herrick, I. R., Um, J., Houk, K. N., Frontier, A. J.  "A torquoselective extrusion of isoxazoline N-oxides. Application to the synthesis of aryl vinyl and divinyl ketones for Nazarov cyclization,"  Tetrahedron  2009653165-3179.
Malona, J. M., Cariou, K., Frontier, A. J.  "Nazarov Cyclization Initiated by Peracid Oxidation: The Total Synthesis of (±)-Rocaglamide,"  J. Am. Chem. Soc.  20091317560-7561.
Bitar, A. Y., Frontier, A. J.  "Formal Synthesis of Roseophilin,"  Org. Lett.  20091149-52.
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.  20081301003-1011.
He, W., Huang, J., Frontier, A. J.  "Total Synthesis of (±)-Merrilactone A,"  J. Am. Chem. Soc.  2008130300-308.
Jiang, C., Frontier, A. J.  "Stereoselective Synthesis of Pyrrolidine Derivatives via Reduction of Substituted Pyrroles,"  Org. Lett.  200794939-4942.
Huang, J., Frontier, A. J.  "Development of a Nazarov Cyclization/ Wagner-Meerwein Rearrangement Sequence for the Stereoselective Synthesis of Spirocycles,"  J. Am. Chem. Soc.  20071298060-8061.
Malona, J. A., Colbourne, J. M., Frontier, A. J.  "A General Method for the Catalytic Nazarov Cyclization of Heteroaromatic Compounds,"  Org. Lett.  200685661-5664.
Janka, M., He, W., Haedicke, I. E., Fronczek, F. R., Frontier, A. J., Flaschenriem, C., Eisenberg, R.  "Tandem Nazarov Cyclization-Michael Addition Sequence Catalyzed by an Ir(III) Complex,"  J. Am. Chem. Soc.  20061285312-5313.
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Professor Frontier's Contact Information...

Office: Hutchison 414
Phone: (585) 275-2568

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