A K+-promoted Diels-Alder reaction by using a self-assembled macrocyclic boronic ester containing two crown ether
Kosuke Ono1, Morikazu Niibe1, Nobuharu Iwasawa1
1Department of Chemistry , Tokyo Institute of Technology , O-okayama, Meguro-ku , Tokyo 152-8551 , Japan .
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] 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.
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Crown Ethers
