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Synthesis 1995; 1995(11): 1427-1431
DOI: 10.1055/s-1995-4107
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Enantioselective Chemoenzymatic Synthesis of the S-Enantiomer of the Systemic Fungicide Fenpropimorph

Amir Avdagić, Mirjana Gelo-Pujić, Vitomir Šunjić*
  • *Ruđer Bošković Institute, P.O.B. 1016, 41001 Zagreb, Croatia, Fax +385(1)425497
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Publication Date:
31 December 2000 (online)

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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.

Completely enantioselective acylation of a prochiral 1,3-diol by Pseudomonas sp. lipase