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

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 journal › Article › peer-review

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.

Original language	English
Pages (from-to)	12-18
Number of pages	7
Journal	Journal of the Mexican Chemical Society
Volume	59
Issue number	1
State	Published - 1 Jan 2015
Externally published	Yes

Keywords

Diastereoisomeric 4-hydroxybutyramides
Phenyl-γ-butyrolactones
Resolution

Cite this

Gómez-Gutiérrez, J., Meléndez-Rodríguez, M., Suárez-Castillo, Ó. R., Castelán-Duarte, L. E., Fragoso-Vázquez, M. J., López-Vázquez, E., & Sánchez-Zavala, M. (2015). Preparation of (+)-and (−)-β-phenyl-and β-(4-chlorophenyl)-γ-butyrolactones: Key intermediates in the synthesis of β-phenyl-GABA and Baclofen. Journal of the Mexican Chemical Society, 59(1), 12-18.

@article{a12acbe2c8a44fc5b1ba8578f7535e93,

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

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{\textquoteright}R,3S)-5, (2{\textquoteright}R,3R)-5, (2{\textquoteright}R,3S)-6 and (2{\textquoteright}R,3R)-6 is described. The absolute configuration assignment of enantiopure 3 and 4 was supported by X-ray crystallographic structures of (2{\textquoteright}R,3R)-5, (2{\textquoteright}R,3S)-6 and (2{\textquoteright}R,3R)-6.",

keywords = "Diastereoisomeric 4-hydroxybutyramides, Phenyl-γ-butyrolactones, Resolution",

author = "Jazm{\'i}n G{\'o}mez-Guti{\'e}rrez and Myriam Mel{\'e}ndez-Rodr{\'i}guez and Su{\'a}rez-Castillo, {{\'O}scar R.} and Castel{\'a}n-Duarte, {Luis E.} and Fragoso-V{\'a}zquez, {Manuel J.} and Erick L{\'o}pez-V{\'a}zquez and Maricruz S{\'a}nchez-Zavala",

note = "Publisher Copyright: {\textcopyright} 2015, Sociedad Qu{\'i}mica de M{\'e}xico.",

year = "2015",

month = jan,

day = "1",

language = "Ingl{\'e}s",

volume = "59",

pages = "12--18",

journal = "Journal of the Mexican Chemical Society",

issn = "1870-249X",

number = "1",

}

Gómez-Gutiérrez, J, Meléndez-Rodríguez, M, Suárez-Castillo, ÓR, Castelán-Duarte, LE, Fragoso-Vázquez, MJ, López-Vázquez, E & Sánchez-Zavala, M 2015, 'Preparation of (+)-and (−)-β-phenyl-and β-(4-chlorophenyl)-γ-butyrolactones: Key intermediates in the synthesis of β-phenyl-GABA and Baclofen', Journal of the Mexican Chemical Society, vol. 59, no. 1, pp. 12-18.

Preparation of (+)-and (−)-β-phenyl-and β-(4-chlorophenyl)-γ-butyrolactones: Key intermediates in the synthesis of β-phenyl-GABA and Baclofen. / Gómez-Gutiérrez, Jazmín; Meléndez-Rodríguez, Myriam; Suárez-Castillo, Óscar R. et al.
In: Journal of the Mexican Chemical Society, Vol. 59, No. 1, 01.01.2015, p. 12-18.

Research output: Contribution to journal › Article › peer-review

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

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 -

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

Abstract

Keywords

Other files and links

Fingerprint

Cite this