Zirconium-Mediated Intramolecular Ester Transfer Reaction: Synthesis of α-Substituted γ-Aminobutyric Acid (GABA) Derivatives

Organic Letters

Volumn 4, Issue 9, 2002, Pages 1499-1501

  Ito, Hisanaka ^a   Omodera, Katsunori ^a   Takigawa, Yasushi ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINOBUTYRIC ACID; DRUG DERIVATIVE; ESTER; LACTAM; ZIRCONIUM;

ARTICLE; CHEMISTRY; SYNTHESIS;

ESTERS; GAMMA-AMINOBUTYRIC ACID; LACTAMS; ZIRCONIUM;

EID: 0037007730     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025709k     Document Type: Article

References (22)

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13. Typical Experimental Procedure for the Intramolecular Ester Transfer Reaction. Under an argon atmosphere, a solution of n-butyllithium (1.48 M in hexane, 0.81 mL, 1.2 mmol) was added to a solution of zirconocene dichloride (175 mg, 0.6 mmol) in THF (2 mL) at -78°C, and the reaction mixture was stirred at the same temperature for 1 h. A solution of compound 3 (0.5 mmol) in THF (2 mL) was added to the reaction mixture at -78°C, and the mixture was stirred at ambient temperature for 1 h. To the reaction mixture was added 4% hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine, and dried over magnesium sulfate. After filtration, the filtrate was concentrated under vacuum. The residue was purified by silica gel column chromatography.
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