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Synthesis 1996; 1996(6): 748-754
DOI: 10.1055/s-1996-4288
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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.

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