Abstract

GOMEZ-GUTIERREZ, Jazmín et al. Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ-butyrolactones: Key Intermediates in the Synthesis of β-phenyl-GABA and Baclofen. J. Mex. Chem. Soc [online]. 2015, vol.59, n.1, pp.12-18. ISSN 1870-249X.

The preparation of β-phenyl- and β-(4-chlorophenyl)-γ-butyrolactones ( ± )-3 and ( ± )-4 and their resolution to the corresponding (+)-(S)-3, (-)-(R)-3 and (+)-(S)-4, (-)-(R)-4 through formation, flash column chromatography separation and subsequent hydrolysis of diastereoisomeric 4-hydroxybutyramides (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2'R,3R)-5, (2'R,3S)-6 and (2'R,3R)-6.

Keywords : Phenyl-γ-butyrolactones; Resolution; Diastereoisomeric 4-hydroxybutyramides.

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