Preparation of (+)- and (?)- ?-phenyl- and ?-(4-chlorophenyl)-?-butyrolactones: Key Intermediates in the Synthesis of ?-phenyl-GABA andBaclofen
Sánchez Zavala, Maricruz
2015
Jazmín Gómez-Gutiérrez, Myriam Meléndez-Rodríguez, Oscar R. Suárez-Castillo, Luis E. Castelán-Duarte, Manuel J. Fragoso-Vázquez, Erick López-Vázquez, Maricruz Sánchez-Zavala, ?Preparation of (+)-and (-)- ?-(4-chlorophenyl)-?-butyrolactones: key intermediates in the synthesis of ?-phenylGABA and Baclofen? Journal of the Mexican Chemical Society, 59, 12-18, (2015).
Abstract
The preparation of ?-phenyl- and ?-(4-chlorophenyl)-?-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 hydrolysisof diastereoisomeric 4-hydroxybutyramides (2?R,3S)-5, (2?R,3R)-5,(2?R,3S)-6 and (2?R,3R)-6 is described. The absolute configurationassignment of enantiopure 3 and 4 was supported by X-ray crystallographicstructures of (2?R,3R)-5, (2?R,3S)-6 and (2?R,3R)-6
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