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Issue 11, 2015
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Cooperative benzylic–oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds

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Abstract

We describe a novel reactivity of benzylic–stabilized oxyallyl cations towards regioselective construction of carbon quaternary centers. These synthetically useful intermediates were readily generated upon ionization of aryl substituted α-hydroxy methylenol ethers with catalytic, mild Brønsted acid. The emerging unsymmetrical oxyallyl cations were then directly captured by indoles and other nucleophiles with exquisite control of regioselectivity, predictably at the electrophilic carbon bearing the alkyl substituent to produce highly functionalized, value-added enol ethers.

Graphical abstract: Cooperative benzylic–oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds

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Publication details

The article was received on 28 May 2015, accepted on 20 Jul 2015 and first published on 22 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC01914A
Citation: Chem. Sci., 2015,6, 6312-6319
  • Open access: Creative Commons BY license
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    Cooperative benzylic–oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds

    N. S. Dange, J. R. Stepherson, C. E. Ayala, F. R. Fronczek and R. Kartika, Chem. Sci., 2015, 6, 6312
    DOI: 10.1039/C5SC01914A

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