Tetrahedron: asymmetry

Preparation of enantiomerically pure (R)-and (S)-3-amino-3-phenyl-1-propanol via resolution with immobilized penicillin G acylase

NW Fadnavis, KR Radhika, AV Devi

Index: Fadnavis, Nitin W.; Radhika, Kasiraman R.; Vedamayee Devi Tetrahedron Asymmetry, 2006 , vol. 17, # 2 p. 240 - 244

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Citation Number: 13

Abstract

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 ...