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Issue 42, 2014
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α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

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Abstract

Trimethylaluminum and molecular oxygen are used in tandem to interrupt the Nazarov cyclization. α-Hydroxycyclopentanones are produced in moderate to good yield as a mixture of epimers. This sequence is the first example of combined nucleophilic/electrophilic trapping of the Nazarov oxyallyl intermediate.

Graphical abstract: α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

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Publication details

The article was received on 28 Mar 2014, accepted on 11 Apr 2014 and first published on 14 Apr 2014


Article type: Communication
DOI: 10.1039/C4CC02330G
Citation: Chem. Commun., 2014,50, 5558-5560
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    α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with triplet oxygen

    Y. Kwon, O. Scadeng, R. McDonald and F. G. West, Chem. Commun., 2014, 50, 5558
    DOI: 10.1039/C4CC02330G

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