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2-chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl)]-1,3,2-dioxaphosp holane: A practical chiral pool-derived reagent for determining enantiomeric purity of alcohols

JOURNAL OF ORGANIC CHEMISTRY. Bd. 73. H. 10. 2008 S. 3907 - 3910

Erscheinungsjahr: 2008

ISBN/ISSN: 0022-3263

Publikationstyp: Zeitschriftenaufsatz

Doi/URN: 10.1021/jo7026068

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Inhaltszusammenfassung


2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl)]-1,3,2-dioxaphosp holane is a practical reagent for reliably determining enantiomeric purity of chiral alcohols via (31)p NMR spectroscopy. The compound is available as a crystalline solid on a 20 g scale from PCl3 and bis[(1R,2S,5R)menth-1-yl] tartrate. It is comparatively inert toward spontaneous hydrolysis under conventional laboratory conditions but undergoes quantitative substitution of alkoxide for chloride if treated with a chiral ...2-Chloro-(4R,5R)-bis[(1R,2S,5R)-menth-1-yloxycarbonyl)]-1,3,2-dioxaphosp holane is a practical reagent for reliably determining enantiomeric purity of chiral alcohols via (31)p NMR spectroscopy. The compound is available as a crystalline solid on a 20 g scale from PCl3 and bis[(1R,2S,5R)menth-1-yl] tartrate. It is comparatively inert toward spontaneous hydrolysis under conventional laboratory conditions but undergoes quantitative substitution of alkoxide for chloride if treated with a chiral alcohol. Nonequivalent (31)p NMR signals of diastereomeric 2-alkoxy-1,3,2-dioxophospholanes were dispersed by similar to 1.4-0.1 ppm. The associated integral ratios reflected enantiomeric purities of preweighted samples of (R)- and (S)-1-phenylethanol, (+)- and (-)menthol, and a set of primary, secondary, and tertiary alcohols with a precision of +/- 0.4-1.0%. » weiterlesen» einklappen

Autoren


Amberg, M (Autor)
Bergstrasser, U (Autor)
Stapf, G (Autor)

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