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Elsevier, Tetrahedron: Asymmetry, 16(27), p. 729-731

DOI: 10.1016/j.tetasy.2016.06.019

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Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

Journal article published in 2016 by Zsolt Galla ORCID, Forró Enikő, Fülöp Ferenc
This paper was not found in any repository, but could be made available legally by the author.
This paper was not found in any repository, but could be made available legally by the author.

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Abstract

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.