Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Optically Active Intermediate from the Degradation of (-)-Laudanosine, a Benzylisoquinoline Alkaloid, with Ethyl Chloroformate

  • Dong-Ung Lee (Department of Biochemistry, Dongguk University) ;
  • W. Wiegrebe (Institute of Pharmacy, University of Regensburg)
  • Published : 1991.08.20
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Abstract

Degradation of (-)-laudanosine, a 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloid, with ethyl chloroformate (ECF) afforded an optically active chloro-carbamate as an intermediate. The reason why this intermediate exhibits an optical activity was investigated by comparison with the reactions of some model compounds with ECF. It may be supposed that the chloride group in a hypothetic carbenium ion intermediate stands very closely to the chiral center, so conserving optical activity. However, a neighboring group effect can not be excluded.

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References

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  1. ChemInform Abstract: Optically Active Intermediate from the Degradation of (-)-Laudanosine, a Benzylisoquinoline Alkaloid, with Ethyl Chloroformate. vol.23, pp.8, 1991, https://doi.org/10.1002/chin.199208303
  2. β-Phenylethylamines and the isoquinoline alkaloids vol.10, pp.5, 1993, https://doi.org/10.1039/np9931000449
  3. (-)-β-Narcotine: A Facile Synthesis and the Degradation with Ethyl Choroformate vol.23, pp.11, 1991, https://doi.org/10.5012/bkcs.2002.23.11.1548