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

Kim, Hyejin; Gerosa, Gabriela; Aronow, Jonas; Kasaplar, Pinar; Ouyang, Jie; Lingnau, Julia B.; Guerry, Paul; Farès, Christophe; List, Benjamin

doi:10.1038/s41467-019-08374-z

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

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

MPS-Authors

Kim, Hyejin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;
Therapeutics & Biotechnology Division, Korea Research Institute of Chemical Technology;

/persons/resource/persons230441

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

/persons/resource/persons228809

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

/persons/resource/persons225801

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

/persons/resource/persons230439

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

/persons/resource/persons202068

Lingnau, Julia B.
Service Department Farès (NMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

Guerry, Paul
Service Department Farès (NMR), 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;

/persons/resource/persons58764

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

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

s41467-019-08374-z(2).pdf
(Postprint), 2MB

Supplementary Material (public)

There is no public supplementary material available

Citation

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.

Cite as: https://hdl.handle.net/21.11116/0000-0003-0CDE-7

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.