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
- 1 June 1996
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1996 (06) , 748-754
- https://doi.org/10.1055/s-1996-4288
Abstract
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.Keywords
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