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Updated: Apr 9, 2026
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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Enantioselective Nazarov Cyclization Catalyzed by a Cinchona Alkaloid Derivative
Yu-Wen Huang1, Alison J Frontier1
1Department of Chemistry, University of Rochester, Rochester, New York 14627, United States.
Abstract:
Nucleophilic catalysts for a 1,6 addition/Nazarov cyclization/elimination sequence were evaluated for their ability to induce enantioselectivity in the electrocyclization step. Of the tertiary amines examined, it was found that a cinchona alkaloid derivative was able to generate substituted 5-hydroxy γ-methylene cyclopentenones with excellent enantioselectivity. The study results suggest that successful cyclization depends upon the ability of the dienyl diketone substrate to readily adopt an s-cis conformation.
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