Synthesis of optically active beta '-hydroxy-beta-enaminoketones via enzymatic resolution of carbinols derived front 3,5-disubstituted isoxazoles

José A. Fuentes, Alicia Maestro, Ana M. Testera, José M. Báñez

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17 Citations (Scopus)

Abstract

The preparation of several enantiomerically pure beta'-hydroxy-beta-enaminoketones from the corresponding isoxazolic carbinols, which have been obtained by enzymatic kinetic resolution of the racemic beta-hydroxy-isoxazoles catalyzed by lipases? is described. The enzymatic transesterification of racemic (+/-)-5-(2-hydroxy-propyl)-3-methylisoxazole 3a, and racemic (+/-)-5-(2-hydroxy-2-p-tolylethyl)-3-methylisoxazole 3d, has been studied with respect to the influence of experimental variables such as the used enzyme, the acylating agent or the solvent on the enantioselectivity of the reaction. After the reductive cleavage of the isoxazolic ring of the enantiopure carbinols, (R)- and (S)-2-amino-4-oxo-2-hepten-6-ol, (R)- and (S)-5, and (R)-2-amino-6-p-tolyl-4-oxo-2-hexen-6-ol, (R)-7 with an enantiomeric excess > 98% were obtained
Original languageEnglish
Pages (from-to)2565-2577
JournalTetrahedron: Asymmetry
Volume11
Issue number12
DOIs
Publication statusPublished - 30 Jun 2000

Keywords

  • BETA-ENAMINO KETONES
  • REGIOSPECIFIC SYNTHESIS
  • BUILDING-BLOCKS
  • DERIVATIVES
  • AMINOENONES

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