Preparation of (+)-and (−)-β-phenyl-and β-(4-chlorophenyl)-γ-butyrolactones: Key intermediates in the synthesis of β-phenyl-GABA and Baclofen

Jazmín Gómez-Gutiérrez, Myriam Meléndez-Rodríguez, Óscar R. Suárez-Castillo, Luis E. Castelán-Duarte, Manuel J. Fragoso-Vázquez, Erick López-Vázquez, Maricruz Sánchez-Zavala

Research output: Contribution to journalArticle

Abstract

© 2015, Sociedad Química de México. 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.
Original languageAmerican English
Pages (from-to)12-18
Number of pages7
JournalJournal of the Mexican Chemical Society
StatePublished - 1 Jan 2015
Externally publishedYes

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