A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles

We report here that polysubstituted cyclopent-2-enols can be constructed by the one-pot reaction of doubly activated cyclopropanes and α-EWG substituted acetonitriles under mild basic conditions a domino-ring-opening-cyclization/deacylation/oxidation sequence. Moreover, the synthetic applications of...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2022-02, Vol.20 (5), p.1095-1102
Main Authors: Han, Xiao-Dan, Peng, Gao-Liang, Xiong, Wei, Gan, Ran, Fu, Jian-Ping, Wu, Lei, Tang, Zhong-Sheng, Hu, Ju-Wu, Wang, Hui-Bin
Format: Article
Language:English
Subjects:
Cyclopropane
Deacylation
Organic compounds
Oxidation
Ring opening
Substitutes
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Summary:We report here that polysubstituted cyclopent-2-enols can be constructed by the one-pot reaction of doubly activated cyclopropanes and α-EWG substituted acetonitriles under mild basic conditions a domino-ring-opening-cyclization/deacylation/oxidation sequence. Moreover, the synthetic applications of these cyclopent-2-enols have been demonstrated in the late-stage derivatization into functionalized cyclopentapyrimidin-4-ones and 2-hydroxy cyclopentanones with good yields.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob02155a