TY  - JOUR
VL  - 27
SP  - 729
UR  - http://publicatio.bibl.u-szeged.hu/10563/
JF  - TETRAHEDRON-ASYMMETRY
ID  - publicatio10563
A1  -  Galla Zsolt
A1  -  Forró Enik?
A1  -  Fülöp Ferenc
AV  - restricted
EP  - 731
N2  - 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.
IS  - 16
N1  - FELTÖLT?: Nonn Melinda - nonn.melinda@pharm.u-szeged.hu
TI  - Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction
SN  - 0957-4166
Y1  - 2016///
ER  -