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

Hyejin Kim, Gabriela Gerosa, Jonas Aronow, Pinar Kasaplar, Jie Ouyang, Julia B. Lingnau, Paul Guerry, Christophe Farès and Benjamin List ()
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Hyejin Kim: Max-Planck-Institut für Kohlenforschung
Gabriela Gerosa: Max-Planck-Institut für Kohlenforschung
Jonas Aronow: Max-Planck-Institut für Kohlenforschung
Pinar Kasaplar: Max-Planck-Institut für Kohlenforschung
Jie Ouyang: Max-Planck-Institut für Kohlenforschung
Julia B. Lingnau: Max-Planck-Institut für Kohlenforschung
Paul Guerry: Max-Planck-Institut für Kohlenforschung
Christophe Farès: Max-Planck-Institut für Kohlenforschung
Benjamin List: Max-Planck-Institut für Kohlenforschung

Nature Communications, 2019, vol. 10, issue 1, 1-6

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-08374-z

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