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V. Samano, J. A. Ray, J. B. Thompson, R. A. Mook, D. K. Jung, C. S. Koble, M. T. Martin, E. C. Bigham, C. S. Regitz, P. L. Feldman and E. E. Boros, “Synthesis of Ultra-Short-Acting Neuromuscular Blocker GW 0430: A Remarkably Stereoand Regioselective Synthesis of Tetrahydroisoquinolinium Chlorofumarates,” Organic Letters, Vol. 1, No. 12, 1999, pp. 1993-1996. doi:10.1021/ol9911573

has been cited by the following article:

• TITLE: Determination of Enantiomeric Composition of Substituted Tetrahydroisoquinolines Based on Derivatization with Menthyl Chloroformate

  AUTHORS: Jan Přech, Václav Matoušek, Jiří Václavík, Jan Pecháček, Kamila Syslová, Petr Šot, Jakub Januščák, Beáta Vilhanová, Marek Kuzma, Petr Kačer

  KEYWORDS: Tetrahydroisoquinolines; Enantiomeric Composition; Derivatization; Menthyl Chloroformate; Gas Chromatography

  JOURNAL NAME: American Journal of Analytical Chemistry, Vol.4 No.3, March 27, 2013

  ABSTRACT: A method for the analysis of the optical purity of a series of chiral substituted tetrahydroisoquinolines (THIQs) was developed. The method is based on pre-column derivatization of the analytes with the derivatization reagent (–)-(1R)-menthyl chloroformate. The derivatization reaction selectively gives diastereomeric carbamates that are resolvable on an achiral non-polar GC column. The developed technique covers variously substituted THIQs, which differ significantly in volatility, steric and electronic properties. In all cases, the resolution factors (R) exceeded the value of 1.5. The method represents a robust way of analysis of mixtures of THIQs, which are often present in various matrixes such as body fluids, tissues and reaction mixtures.