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  A multi-substrate screening approach for the identification of a broadly applicable Diels–Alder catalyst

Kim, H., Gerosa, G., Aronow, J., Kasaplar, P., Ouyang, J., Lingnau, J. B., et al. (2019). A multi-substrate screening approach for the identification of a broadly applicable Diels–Alder catalyst. Nature Communications, 10: 770. doi:10.1038/s41467-019-08374-z.

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 Creators:
Kim, Hyejin1, 2, Author
Gerosa, Gabriela1, Author              
Aronow, Jonas1, Author              
Kasaplar, Pinar1, Author              
Ouyang, Jie1, Author              
Lingnau, Julia B.3, Author              
Guerry, Paul3, Author
Farès, Christophe3, Author              
List, Benjamin1, Author              
Affiliations:
1Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445585              
2Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology, 34114, Daejeon, Republic of Korea, ou_persistent22              
3Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445623              

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 Abstract: When developing a synthetic methodology, chemists generally optimize a single substrate and then explore the substrate scope of their method. This approach has led to innumerable and widely-used chemical reactions. However, it frequently provides methods that only work on model substrate-like compounds. Perhaps worse, reaction conditions that would enable the conversion of other substrates may be missed. We now show that a different approach, originally proposed by Kagan, in which a collection of structurally distinct substrates are evaluated in a single reaction vessel, can not only provide information on the substrate scope at a much earlier stage in methodology development, but even lead to a broadly applicable synthetic methodology. Using this multi-substrate screening approach, we have identified an efficient and stereoselective imidodiphosphorimidate organocatalyst for scalable Diels–Alder reactions of cyclopentadiene with different classes of α,β-unsaturated aldehydes.

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Language(s): eng - English
 Dates: 2018-09-272019-01-082019-02-15
 Publication Status: Published online
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1038/s41467-019-08374-z
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Title: Nature Communications
  Abbreviation : Nat. Commun.
Source Genre: Journal
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Publ. Info: London : Nature Publishing Group
Pages: - Volume / Issue: 10 Sequence Number: 770 Start / End Page: - Identifier: ISSN: 2041-1723
CoNE: https://pure.mpg.de/cone/journals/resource/2041-1723