Naslov
Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph

Autori
Avdagić, Amir ; Gelo-Pujić, Mirjana ; Šunjić, Vitomir

Izvornik
Synthesis (0039-7881) 11 (1995); 1427-1431

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Pseudomonas sp. lipase; monoacetilation; fenpropimorph

Sažetak
Chemoenzymatic synthesis of the S-(-)-enantiomer of fenpropimorph (S)-1 in high optical and chemical purity is described. One feature of this process entails the enantioselective acetylation of prochiral 1, 3-propanediol 4 by Pseudomonas sp. lipases, and subsequent transformation of the monoacetate (R)-5 into the final product by the selected order of transformations that comprise ; chlorination or tosylation under non-racemizing conditions, hydrogenolysis of the resulting chloromethyl or tosyl group in (+)-6 and (+)-8, second chlorination of(-)-9, and alkylation of cis-3, 5-dimethylmorpholine by 1-chloropropane derivative (+)-10. This sequence of reactions affords (S)-1, the more active enantiomer in the commercialized racemic mixture with systemic fungicidal activity.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA