Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ-butyrolactones: key intermediates in the synthesis of β-phenyl-GABA and baclofen
Document title: Preparation of (+)- and (-)- β-phenyl- and β-(4-chlorophenyl)-γ-butyrolactones: key intermediates in the synthesis of β-phenyl-GABA and baclofen
Journal: Journal of the Mexican Chemical Society
Database: PERIÓDICA
System number: 000384129
ISSN: 1665-9686
Authors: 1
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Institutions: 1Universidad Autónoma del Estado de Hidalgo, Area Académica de Química, Pachuca, Hidalgo. México
Year:
Season: Ene-Mar
Volumen: 59
Number: 1
Country: México
Language: Inglés
Document type: Artículo
Approach: Experimental, analítico
Spanish abstract Se describe la preparación de las β-fenil- y β-(4-clorofenil)-γ-butirolactonas (±)-3 y (±)-4 y su resolución en (+)-(S)-3, (-)-(R)-3 y (+)-(S)-4, (-)-(R)-4 mediante la formación, separación por cromatografía en columna rápida y posterior hidrólisis de las 4-hidroxibutiramidas diastereoisoméricas (2'R,3S)-5, (2'R,3R)-5, (2'R,3S)-6 y (2'R,3R)-6. La asignación de la configuración absoluta de las lactonas enantiopuras 3 y 4 se confirmó mediante cristalografía de rayos-X de (2'R,3R)-5, (2'R,3S)-6 y (2'R,3R)-6
English abstract 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
Disciplines: Química
Keyword: Química orgánica,
Fenil-γ-butirolactonas,
Resolución,
Diasteroisómeros
Keyword: Chemistry,
Organic chemistry,
Phenyl-γ-butyrolactones,
Resolution,
Diastereoisomers
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