A K-promoted Diels-Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether moieties

A K + -promoted Diels-Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester [2+2] crown containing two crown ether moieties. The reaction rate is remarkably accelerated (up to 206-fold) compared to that in the absence...

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Veröffentlicht in:Chemical science (Cambridge) 2019, Vol.1 (32), p.7627-7632
Hauptverfasser: Ono, Kosuke, Niibe, Morikazu, Iwasawa, Nobuharu
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Sprache:eng
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Zusammenfassung:A K + -promoted Diels-Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester [2+2] crown containing two crown ether moieties. The reaction rate is remarkably accelerated (up to 206-fold) compared to that in the absence of the promoter. Furthermore, the reaction proceeds regioselectively to yield an internal adduct. The self-assembly protocol was also demonstrated. A K + -promoted Diels-Alder reaction of 1,4,9,10-anthradiquinone with various dienes is achieved in the presence of a self-assembled macrocyclic boronic ester.
ISSN:2041-6520
2041-6539
DOI:10.1039/c9sc01597c