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

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.

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anie.202000307.pdf (Postprint), 4MB
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 Creators:
Ghosh, Santanu1, Author           
Das, Sayantani1, Author           
De, Chandra Kanta1, Author           
Yepes, Diana2, Author           
Neese, Frank3, Author           
Bistoni, Giovanni2, Author           
Leutzsch, Markus4, Author           
List, Benjamin1, Author           
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Research Group Bistoni, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541703              
3Research Department Neese, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_2541710              
4Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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Free keywords: Brønsted acids; cyclohexadienones; Diels–Alder reaction; imidodiphosphorimidates; organocatalysis
 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

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Language(s): eng - English
 Dates: 2020-01-072020-02-032020-03-112020-07-20
 Publication Status: Published in print
 Pages: 5
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/anie.202000307
 Degree: -

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Title: Angewandte Chemie International Edition
  Abbreviation : Angew. Chem., Int. Ed.
Source Genre: Journal
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Publ. Info: Weinheim : Wiley-VCH
Pages: - Volume / Issue: 59 (30) Sequence Number: - Start / End Page: 12347 - 12351 Identifier: ISSN: 1433-7851
CoNE: https://pure.mpg.de/cone/journals/resource/1433-7851