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Issue 0, 1986
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Tetrahydroisoquinolines. Part 2. Synthesis of 4-substituted N-methyl-1,2,3,4-tetrahydroisoquinolines via regio- and stereo-selective elaboration of tricarbonyl(N-methyl-1,2,3,4-tetrahydroisoqumoline)chromium

Abstract

Thermolysis of hexacarbonylchromium with N-methyltetrahydroisoquinoline generates the tricarbonyl-(N-methyltetrahydroisoquinoline)chromium complex (4). The 4-exo proton of complex (4) can be regio- and stereo-selectively removed with butyl-lithium and replaced stereoselectivity with retention of configuration by a variety of electrophiles [Mel, Etl, PhCH2Br, CD3OD, Cr(CO)3(PhF), MoOPH, Me2CO]. Oxidative decomplexation generates quantitatively the corresponding 4-methyl, ethyl, benzyl, deuterio, phenyl, hydroxy, and (1-hydroxy-1-methylethyl)-N-methyltetrahydroisoquinolines.

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Article type: Paper
DOI: 10.1039/P19860002257
Citation: J. Chem. Soc., Perkin Trans. 1, 1986,0, 2257-2261
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    Tetrahydroisoquinolines. Part 2. Synthesis of 4-substituted N-methyl-1,2,3,4-tetrahydroisoquinolines via regio- and stereo-selective elaboration of tricarbonyl(N-methyl-1,2,3,4-tetrahydroisoqumoline)chromium

    J. Blagg, S. J. Coote, S. G. Davies and B. E. Mobbs, J. Chem. Soc., Perkin Trans. 1, 1986, 0, 2257
    DOI: 10.1039/P19860002257

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