Strong and Confined Acids Control Five Stereogenic Centers in Catalytic 
Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene

Ghosh, Santanu; Das, Sayantani; De, Chandra Kanta; Yepes, Diana; Neese, Frank; Bistoni, Giovanni; Leutzsch, Markus; List, Benjamin

doi:10.1002/anie.202000307

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Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene

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

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

/persons/resource/persons132969

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

/persons/resource/persons216846

Yepes, Diana
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216825

Neese, Frank
Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

/persons/resource/persons216804

Bistoni, Giovanni
Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Leutzsch, Markus
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

Ghosh, S., Das, S., De, C. K., Yepes, D., Neese, F., Bistoni, G., et al. (2020). Strong and Confined Acids Control Five Stereogenic Centers in Catalytic Asymmetric Diels–Alder Reactions of Cyclohexadienones with Cyclopentadiene. Angewandte Chemie International Edition, 59(30), 12347-12351. doi:10.1002/anie.202000307.

Cite as: https://hdl.handle.net/21.11116/0000-0006-B431-7

Abstract

We describe a highly enantioselective Diels–Alder reaction of cross‐conjugated cyclohexadienones with cyclopentadiene, in which five stereocenters are effectively controlled by a strongly acidic and confined imidodiphosphorimidate catalyst. Our approach provides tricyclic products in excellent stereoselectivity. We also report methods to convert the obtained products into useful intermediates and a computational study that aids in gaining deeper insight into the reaction mechanism and origin of stereoselectivity