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Issue 21, 2016
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Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench

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Abstract

Substituted N-tert-butoxycarbonyl (Boc)-1,2,3,4-tetrahydroisoquinolines were prepared and treated with n-butyllithium in THF at −50 °C to test the scope of the metallation and electrophilic quench. The lithiation was optimised by using in situ ReactIR spectroscopy and the rate of rotation of the carbamate was determined. The 1-lithiated intermediates could be trapped with a variety of electrophiles to give good yields of 1-substituted tetrahydroisoquinoline products. Treatment with acid or reduction with LiAlH4 allows conversion to the N–H or N–Me compound. The chemistry was applied to the efficient total syntheses of the alkaloids (±)-crispine A and (±)-dysoxyline.

Graphical abstract: Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench

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Publication details

The article was received on 16 Mar 2016, accepted on 04 May 2016 and first published on 04 May 2016


Article type: Paper
DOI: 10.1039/C6OB00577B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2016,14, 4908-4917
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    Synthesis of substituted tetrahydroisoquinolines by lithiation then electrophilic quench

    R. A. Talk, A. Duperray, X. Li and I. Coldham, Org. Biomol. Chem., 2016, 14, 4908
    DOI: 10.1039/C6OB00577B

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