| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1348673 | Tetrahedron: Asymmetry | 2006 | 5 Pages |
Ethyl 2,4-dioxo-4-phenylbutyrate, obtained by condensation of acetophenone with diethyl oxalate, was converted to 3-oxo-3-phenyl-1-propanol in 90% yield by reaction with baker’s yeast. Reductive amination with sodium cyanoborohydride in the presence of ammonium acetate gave the racemic 3-amino-3-phenyl-1-propanol in 65% yield. Enzymatic resolution of the corresponding N-phenylacetyl derivative with penicillin G acylase, immobilized on an epoxy resin gave (S)-amide and (R)-amino alcohol in high enantiomeric purity (ee >99%) and >45% yields for each enantiomer.
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(R)-3-Amino-3-phenyl-1-propanolC9H13NOEe >99%[α]D25=+2.8 (c 0.57, ethanol)Source of chirality: enzymatic resolutionAbsolute configuration: (R)
(R)-3-Amino-3-phenyl-1-propanol hydrochlorideC9H14ClNOEe >99%[α]D25=-30.6 (c 1, ethanol)Source of chirality: enzymatic resolutionAbsolute configuration: (R)
(S)-3-Amino-3-phenyl-1-propanolC9H13NOEe >99%[α]D25=-2.75 (c 0.57, ethanol)Source of chirality: enzymatic resolutionAbsolute configuration: (S)
(S)-3-Amino-3-phenyl-1-propanol hydrochlorideC9H14ClNOEe >99%[α]D25=+30.5 (c 1, ethanol)Source of chirality: enzymatic resolutionAbsolute configuration: (S)
(S)-3-[N-(Phenylacetyl)amino]-3-phenyl-1-propanolC17H19NO2Ee >99%[α]D25=-51.6 (c 1, ethanol)Source of chirality: enzymatic resolutionAbsolute configuration: (S)
