Preparation of (+)- and (−)- β-phenyl- and β-(4-chlorophenyl)-γ- butyrolactones: Key Intermediates in the Synthesis of β-phenyl-GABA and Baclofen
DOI:
https://doi.org/10.29356/jmcs.v59i1.8Keywords:
Phenyl-ï§-butyrolactones, resolution, diastereoisomeric 4-hydroxybutyramidesAbstract
The preparation of b-phenyl- and b-(4-chlorophenyl)-g-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.Downloads
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