%0 Journal Article
%@ 0957-4166
%A  Galla Zsolt
%A  Forró Enikő
%A  Fülöp Ferenc
%A SZTE/GYTK/Gyógyszerkémiai Intézet,
%D 2016
%F publicatio:10563
%J TETRAHEDRON-ASYMMETRY
%N 16
%P 729-731
%T Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction
%U http://publicatio.bibl.u-szeged.hu/10563/
%V 27
%X A very efficient enzymatic two-step cascade reaction was devised (E > 200) for the resolution of activated gamma-lactams (+/-)-1 and (+/-)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5 equiv) in the presence of benzylamine (1 equiv) in i-Pr2O at 60 degrees C. The ring-opened enantiomerically pure gamma-amino acids (1S,4R)-6 (ee = 99%, intermediate of abacavir) and (1S,3R)-8 (ee = 99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee >= 96%) were obtained in good yields (>= 43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6 center dot HCl and (1S,3R)-8 center dot HCI or (15,4R)-3 and (1R,4S)-4 quantitatively, with ee >= 96%. (C) 2016 Elsevier Ltd. All rights reserved.
%Z FELTÖLTŐ: Nonn Melinda - nonn.melinda@pharm.u-szeged.hu