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A General Method for the Catalytic Nazarov Cyclization of Heteroaromatic Compounds

John A. Malona, Jessica M. Colbourne and Alison J. Frontier*

*Department of Chemistry, University of Rochester, Rochester, New York, 14627, Email: frontierchem.rochester.edu

J. A. Malona, J. M. Colbourne, A. J. Frontier, Org. Lett., 2006, 8, 5661-5664.

DOI: 10.1021/ol062403v (free Supporting Information)


Abstract

Scandium triflate was identified as the most reactive promoter for efficient catalytic Nazarov cyclization of systems containing heteroaromatic components and it was found that addition of lithium perchlorate was necessary for synthetically useful catalytic cyclizations. The method was used to synthesize a range of cyclopentanone-fused heteroaromatic systems in good yield.

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Cationic Cyclizations and Rearrangements Promoted by a Heterogeneous Gold Catalyst

T. Vaidya, R. Cheng, P. N. Carlsen, A. J. Frontier, R. Eisenberg, Org. Lett., 2014, 16, 800-803.


Key Words

Nazarov Cyclization


ID: J54-Y2006-3860