PDF herunterladen
Synthesis 1996; 1996(6): 748-754
DOI: 10.1055/s-1996-4288
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Enzymes in Organic Chemistry, Part 4: Enantioselective Hydrolysis of 1-Acyloxy(aryl)methyl- and 1-Acyloxy(heteroaryl)methylphosphonates with Lipases from Aspergillus niger and Rhizopus oryzae. A Comparative Study

Gerhard Eidenhammer, Friedrich Hammerschmidt*
  • *Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria, Fax +43(1)313672280
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

Racemic 1-acyloxy(aryl)methyl- and 1-acyloxy(heteroaryl)methylphosphonates (±)-4 are prepared and tested for kinetic resolution by lipases AP 6 and FAP 15. Both enzymes proved to be useful in terms of broadness of application, reaction rate and enantiomeric excess. In general, reaction rates are higher with lipase AP 6 than with FAP 15. (S)-α-Hydroxyphosphonates (-)-3 are formed on enzymatic hydrolysis of α-acyloxyphosphonates (±)-4. Lipase FAP 15 gives products with higher enantiomeric excesses. 1-Acetoxy-(2-methoxyphenyl)methylphosphonates are either not kinetically resolved or are saponified with very low enantioselectivity.

Optically active α-hydroxy(aryl)- and α-hydroxy(heteroaryl)methylphosphonates are prepared using lipases.