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Issue 24, 2017
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Tryptophan/copper-catalyzed aromatization reaction of chiral cyclohexanones to phenols

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Abstract

By merging organocatalysis with copper catalysis, a highly efficient stereospecific approach for the synthesis of chiral phenols from cyclohexanones has been developed for the first time. The aromatization reaction proceeds through the in situ formation of enone intermediates and further subsequent bromination/dehydrobromination reactions. And a series of functionalized phenol derivatives are obtained in good yields (up to 89%) and good to excellent enantioselectivities (up to 99% ee).

Graphical abstract: Tryptophan/copper-catalyzed aromatization reaction of chiral cyclohexanones to phenols

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Publication details

The article was received on 06 May 2017, accepted on 30 May 2017 and first published on 31 May 2017


Article type: Communication
DOI: 10.1039/C7OB01114H
Citation: Org. Biomol. Chem., 2017,15, 5126-5130
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    Tryptophan/copper-catalyzed aromatization reaction of chiral cyclohexanones to phenols

    X. Liu, X. Zhang, A. Xia, Y. Guo, C. Meng and D. Xu, Org. Biomol. Chem., 2017, 15, 5126
    DOI: 10.1039/C7OB01114H

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