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Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of ?-quaternary centers in ketone-derived compounds.

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 ?-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.

SUBMITTER: Dange NS 

PROVIDER: S-EPMC6054113 | biostudies-other | 2015 Nov

REPOSITORIES: biostudies-other

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

Dange Nitin S NS   Stepherson Jacob R JR   Ayala Caitlan E CE   Fronczek Frank R FR   Kartika Rendy R  

Chemical science 20150722 11

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 t  ...[more]

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