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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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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cited_by cdi_FETCH-LOGICAL-c315t-3616f7782f6f3cd6ba6d11f9ba2d508850430479a69910d4986c435587911f143
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container_title Organic & biomolecular chemistry
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creator Han, Xiao-Dan
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description 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.
doi_str_mv 10.1039/d1ob02155a
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source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Cyclopropane
Deacylation
Organic compounds
Oxidation
Ring opening
Substitutes
title A base-mediated aerobic oxidative synthesis of cyclopent-2-enol derivatives from doubly activated cyclopropanes and substituted acetonitriles
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