The biocatalytic oxidation of racemic O-S-dimethyl O-p-nitrophenyl phosphorodithioate 5 catalyzed by chloroperoxidase from Caldariomyces fumago resulted in the formation of the (-)-(S)-enantiomer of the corresponding oxon 4 and unoxidized substrate 5 with a (+)-(R)-configuration. Both compounds were obtained with very high enantiomeric excesses, 99.6% and 97%, respectively. The thionation reaction of the resulting (-)-(S)-oxon 4 with Lawesson's reagent gave (-)-(S)-phosphorodithioate 5 with full stereoselectivity, while the oxidation of unreacted substrate (+)-(R)-5 with iodoxybenzene afforded oxon (+)-(R)-4 with 94.9% ee.

Biocatalytic oxidation of thiophosphoryl compounds : a new chemo-enzymatic approach to enantiomeric insecticidal thionophosphates and their oxons / M. Mikolajczyk, J. Luczak, P. Kielbasinski, S. Colonna. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 20:16(2009), pp. 1948-1951. [10.1016/j.tetasy.2009.07.031]

Biocatalytic oxidation of thiophosphoryl compounds : a new chemo-enzymatic approach to enantiomeric insecticidal thionophosphates and their oxons

S. Colonna
Ultimo
2009

Abstract

The biocatalytic oxidation of racemic O-S-dimethyl O-p-nitrophenyl phosphorodithioate 5 catalyzed by chloroperoxidase from Caldariomyces fumago resulted in the formation of the (-)-(S)-enantiomer of the corresponding oxon 4 and unoxidized substrate 5 with a (+)-(R)-configuration. Both compounds were obtained with very high enantiomeric excesses, 99.6% and 97%, respectively. The thionation reaction of the resulting (-)-(S)-oxon 4 with Lawesson's reagent gave (-)-(S)-phosphorodithioate 5 with full stereoselectivity, while the oxidation of unreacted substrate (+)-(R)-5 with iodoxybenzene afforded oxon (+)-(R)-4 with 94.9% ee.
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/143423
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