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Issue 12, 1989
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Enantiospecific synthesis of (+)-(R)-6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline from (+)-(S)-2-methylamino-1-phenylethanol (halostachine)

Abstract

Acid-promoted cyclisation of (+)-(R)-N-(3,4-dimethoxybenzyl)halostachine tricarbonylchromium at –20 °C is highly stereoselective, proceeding with retention of configuration, to yield, after removal of the tricarbonylchromium unit, homochiral (+)-(R)-6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4tetrahydroisoquinoline. In contrast, cyclisation of (–)-(R)-N-(3,4-dimethoxybenzyl)halostachine under acidic conditions at –20 °C showed poor stereoselectivity giving predominantly the tetrahydroisoquinoline product corresponding to inversion of configuration, (+)-(R)-6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline, with an e.e. of 54%.

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Article type: Paper
DOI: 10.1039/P19890002223
Citation: J. Chem. Soc., Perkin Trans. 1, 1989,0, 2223-2228
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    Enantiospecific synthesis of (+)-(R)-6,7-dimethoxy-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline from (+)-(S)-2-methylamino-1-phenylethanol (halostachine)

    S. J. Coote, S. G. Davies, D. Middlemiss and A. Naylor, J. Chem. Soc., Perkin Trans. 1, 1989, 0, 2223
    DOI: 10.1039/P19890002223

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