TY - JOUR
T1 - Preparation of enantiomerically pure (R)- and (S)-3-amino-3-phenyl-1- propanol via resolution with immobilized penicillin G acylase
AU - Fadnavis, Nitin W.
AU - Radhika, Kasiraman R.
AU - Vedamayee Devi, A.
N1 - Funding Information:
We thank CSIR, New Delhi, for grant of SRF to K.R.R. and financial support.
PY - 2006/1/23
Y1 - 2006/1/23
N2 - 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.
AB - 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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U2 - 10.1016/j.tetasy.2005.12.022
DO - 10.1016/j.tetasy.2005.12.022
M3 - Article
AN - SCOPUS:32444446803
SN - 0957-4166
VL - 17
SP - 240
EP - 244
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 2
ER -