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Zur Synthese von (±)-cis-1,2-Epoxy-3-oxo-alkyl-phosphonsäureestern—Phosphonomycinanaloga

Synthesis of dialkyl (±)-cis-1,2-epoxy-3-oxoalkylphosphonates—Phosphonomycinanalogues

  • Organische Chemie Und Biochemie
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Abstract

Treatment of dialkyl-3-oxo-1-alkenylphosphonates1 with OsO4-H2O2 affords the (±)-threo-glycols2, which were characterised as their corresponding diacetates3. The derivatives2 were transformed into the mono-(tert-butyl-dimethylsilylether)-compounds4 and5. Subsequent treatment withp-toluene-sulfonyl chloride yields6 and7, which can be converted to (±)-cis-1,2-epoxy-3-oxoalkylphosphonates8 with tetrabutylammonium fluoride (TBAF). Sometimes thetrans-derivatives9 can be found just as the tosyloxyphosphonates11 and12 as by-products. In two cases the 1,2-dicarbonyl compounds10 were obtained.

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  1. Institut für Organische Chemie, Universität Wien, A-1090, Wien, Österreich

    Gottfried Penz & Erich Zbiral

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  1. Gottfried Penz
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Herrn Kollegen Prof. Dr.E. Ziegler zum 70. Geburtstag gewidmet.

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Penz, G., Zbiral, E. Zur Synthese von (±)-cis-1,2-Epoxy-3-oxo-alkyl-phosphonsäureestern—Phosphonomycinanaloga. Monatsh Chem 113, 1169–1190 (1982). https://doi.org/10.1007/BF00808631

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