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Synthese von Phosphonoäpfelsäureestern durch Reduktion von 3-Phosphonopyruvaten

Synthesis of phosphono-hydroxyesters by reduction of phosphonopyruvates

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Summary

The reduction of 3-phosphonopyruvates with ammonia-borane complex proceeds with a very high diastereoselectivity (25:1).Syn- andanti-diastereoisomeric hydroxy esters could be unambiguously assigned by NMR spectroscopy. Furthermore, other β-ketophosphonates could easily be reduced. Thus, diethyl-3,3-diethoxy-2-hydroxybutyl phosphonate was obtained which gave diethyl-2-hydroxy-3-oxobutyl phosphonate after hydrolysis the first known phosphonoacyloine.

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Literatur

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Authors and Affiliations

  1. Pharmazeutisch-Chemisches Institut der Universität Heidelberg, D-69120, Heidelberg, Germany

    R. Neidlein & H. Feistauer

Authors
  1. R. Neidlein
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  2. H. Feistauer
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Herrn Prof.W. Fleischhacker, Wien, mit den besten Wünschen zum 65. Geburtstag gewidmet.

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Neidlein, R., Feistauer, H. Synthese von Phosphonoäpfelsäureestern durch Reduktion von 3-Phosphonopyruvaten. Monatsh Chem 128, 37–52 (1997). https://doi.org/10.1007/BF00807637

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  • DOI: https://doi.org/10.1007/BF00807637

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