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

ABSTRACT: 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.

SUBMITTER: Ono K

PROVIDER: S-EPMC6761878 | biostudies-other | 2019 Aug

REPOSITORIES: biostudies-other

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

Ono Kosuke K Niibe Morikazu M Iwasawa Nobuharu N

Chemical science 20190703 32

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. ...[more]

PMID: 31588314

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