Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of 
Simple Divinyl Ketones

Ouyang, Jie; Kennemur, Jennifer L.; De, Chandra Kanta; Farès, Christophe; List, Benjamin

doi:10.1021/jacs.8b13899

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Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones

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Ouyang, Jie
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Kennemur, Jennifer L.
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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De, Chandra Kanta
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons58537

Farès, Christophe
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Ouyang, J., Kennemur, J. L., De, C. K., Farès, C., & List, B. (2019). Strong and Confined Acids Enable a Catalytic Asymmetric Nazarov Cyclization of Simple Divinyl Ketones. Journal of the American Chemical Society, 141(8), 3414-3418. doi:10.1021/jacs.8b13899.

Cite as: https://hdl.handle.net/21.11116/0000-0004-4362-2

Abstract

We report a catalytic asymmetric Nazarov cyclization of simple, acylic, alkyl-substituted divinyl ketones using our recently disclosed strong and confined imidodiphosphorimidate Brønsted acids. The corresponding monocyclic cyclopentenones are formed in good yields and excellent regio-, diastereo-, and enantioselectivities. Further, the chemical utility of the obtained enantiopure cyclopentenones is demonstrated.