Abstract

Twelve new chiral chelating resins have been prepared using solid phase organic synthesis with the Merrifield and Wang resins and the bidentate amine 1,2-ethylenediamine, followed by the coupling of asymmetric ketones such as 1-phenyletanone, 4-methyl-2-pentanone 4-nitroacetophenone and 4-methoxyacetophenone to form prochiral imines. The enantioselective reduction with borane and (R)-(+)-2-Methyl-CBS-oxazaborolidine leads to the chiral resins with yields greater than 86%. We used these chiral resins to prepare 24 reducing complexes with alkali tetrahydroborates in a very simple way giving yields greater than 87%. Finally, we achieved a preliminary enantioselective reduction of acetophenone employing the Merrifield's chiral chelating resins obtaining the corresponding S alcohol in a 70:30 ratio with the R analog alcohol.
Original languageEnglish
Pages (from-to)8776-8780
Number of pages5
JournalChemistrySelect
Volume4
Issue number30
DOIs
StatePublished - 2019

Keywords

  • Chiral amines
  • Imines
  • Reducing Agents
  • Solid phase
  • Tetrahydroborates

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