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Occhiato, Ernesto G.; De Marchi, Elisa; Arnodo, Davide; Maffeis, Elia; Scarpi, Dina; Prandi, Cristina

Enantiodivergent Synthesis of Halofuginone by Candida antarctica Lipase B (CAL-B)-Catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)

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  • Medientyp: E-Artikel
  • Titel: Enantiodivergent Synthesis of Halofuginone by Candida antarctica Lipase B (CAL-B)-Catalyzed Kinetic Resolution in Cyclopentyl Methyl Ether (CPME)
  • Beteiligte: Occhiato, Ernesto G.; De Marchi, Elisa; Arnodo, Davide; Maffeis, Elia; Scarpi, Dina; Prandi, Cristina
  • Erschienen: Georg Thieme Verlag KG, 2021
  • Erschienen in: SynOpen
  • Sprache: Englisch
  • DOI: 10.1055/a-1523-6428
  • ISSN: 2509-9396
  • Schlagwörter: Organic Chemistry ; Materials Science (miscellaneous) ; Biomaterials ; Catalysis
  • Entstehung:
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  • Beschreibung: <jats:title>Abstract</jats:title><jats:p>The synthesis of both enantiomers of a key intermediate in the synthesis of halofuginone was accomplished by a Candida antarctica lipase B (CAL-B)-catalyzed kinetic resolution of the corresponding racemate. When the resolution was carried out in the versatile solvent cyclopentyl methyl ether (CPME) using p-chlorophenylbutyrate (PCPB) as the acylating reagent, the highest enantiomeric ratio (E) values were measured, and highly enantioenriched (95% ee) compounds could be obtained in a single iteration. As an example, one of the two enantiomers was used as a starting material to prepare (+)-halofuginone in a three-step procedure.</jats:p>
  • Zugangsstatus: Freier Zugang