TY - JOUR
T1 - Preparation of (+)-and (−)-β-phenyl-and β-(4-chlorophenyl)-γ-butyrolactones
T2 - Key intermediates in the synthesis of β-phenyl-GABA and Baclofen
AU - Gómez-Gutiérrez, Jazmín
AU - Meléndez-Rodríguez, Myriam
AU - Suárez-Castillo, Óscar R.
AU - Castelán-Duarte, Luis E.
AU - Fragoso-Vázquez, Manuel J.
AU - López-Vázquez, Erick
AU - Sánchez-Zavala, Maricruz
N1 - Publisher Copyright:
© 2015, Sociedad Química de México.
PY - 2015/1/1
Y1 - 2015/1/1
N2 - 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.
AB - 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.
KW - Diastereoisomeric 4-hydroxybutyramides
KW - Phenyl-γ-butyrolactones
KW - Resolution
UR - http://www.scopus.com/inward/record.url?scp=84939508636&partnerID=8YFLogxK
M3 - Artículo
SN - 1870-249X
VL - 59
SP - 12
EP - 18
JO - Journal of the Mexican Chemical Society
JF - Journal of the Mexican Chemical Society
IS - 1
ER -