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Issue 9, 2018
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Grignard-mediated rearrangement of trifluoroacetyl from dihydroisoquinoline enamides to afford tertiary trifluoromethylcarbinols

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Abstract

Treatment of the trifluoroacetyl enamides of dihydroisoquinolines 2 with diverse Grignard reagents afforded tertiary trifluoromethyl-carbinols 4 by facilitating the addition of tertiary carbinols to the β-carbon of enamides 2. Based on the confirmed formation of vinylogous amides 3, the transformation likely proceeds via unique acyl group rearrangement to the β-carbon of the enamide and subsequent nucleophilic addition of the Grignard reagent. Given the synthetic utility and novelty of this reaction, this work may open new avenues for the synthesis of pharmaceutically important tertiary trifluoromethylcarbinols on cyclic enamide systems.

Graphical abstract: Grignard-mediated rearrangement of trifluoroacetyl from dihydroisoquinoline enamides to afford tertiary trifluoromethylcarbinols

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Publication details

The article was received on 12 Dec 2017, accepted on 05 Feb 2018 and first published on 05 Feb 2018


Article type: Communication
DOI: 10.1039/C7OB03079G
Citation: Org. Biomol. Chem., 2018,16, 1452-1456
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    Grignard-mediated rearrangement of trifluoroacetyl from dihydroisoquinoline enamides to afford tertiary trifluoromethylcarbinols

    R. Achary, G. R. Mathi, S. Kim, J. Y. Hwang and P. Kim, Org. Biomol. Chem., 2018, 16, 1452
    DOI: 10.1039/C7OB03079G

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