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Issue 0, 1987
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Tetrahydroisoquinolines. Part 3. Stereoselective synthesis of cis- and trans-1,4-disubstituted N-methyl-1,2,3,4-tetrahydroisoquinolines as their tricarbonylchromium complexes

Abstract

The 1-exo proton of tricarbonyl-4-exo-methyl- or tricarbonyl-4-exo-ethyl-2-methyl-1,2,3,4-tetrahydroisoquinolinechromium (6) and (7) can be regio- and stereo-selectively removed by t-butyl-lithium and replaced with a variety of electrophiles to give cis-1,4-disubstituted 2-methyl-1,2,3,4-tetrahydroisoquinoline complexes. Oxidative decomplexation generates the corresponding cis-1,4-disubstituted tetrahydroisoquinolines. Similar methodology applied to tricarbonyl (4-exo-trimethylsilyl-2-methyl-1,2,3,4-tetrahydroisoquinoline)chromium (15) gives, after desilylation, 1-exo-substituted tetrahydroisoquinoline complexes.

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Article type: Paper
DOI: 10.1039/P19870000689
Citation: J. Chem. Soc., Perkin Trans. 1, 1987,0, 689-694
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    Tetrahydroisoquinolines. Part 3. Stereoselective synthesis of cis- and trans-1,4-disubstituted N-methyl-1,2,3,4-tetrahydroisoquinolines as their tricarbonylchromium complexes

    J. Blagg, S. J. Coote, S. G. Davies, D. Middlemiss and A. Naylor, J. Chem. Soc., Perkin Trans. 1, 1987, 0, 689
    DOI: 10.1039/P19870000689

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