123557-91-5Relevant academic research and scientific papers
First asymmetric organocatalyzed domino Friedel-Crafts/lactonization reaction in the enantioselective synthesis of the GABAB receptor modulator (S)-BHFF
Vetica, Fabrizio,De Figueiredo, Renata Marcia,Cupioli, Emilia,Gambacorta, Augusto,Loreto, M. Antonietta,Miceli, Martina,Gasperi, Tecla
, p. 750 - 753 (2016)
An asymmetric domino Friedel-Crafts/lactonization sequence between phenols and trifluoropyruvate has been accomplished for the first enantioselective synthesis of (S)-BHFF, a positive allosteric modulator (PAM) of GABAB receptor. The developed protocol leads to 3-OH-benzofuranone derivatives bearing a quaternary stereogenic center, and gives a valuable access to bioactive compounds with promising pharmaceutical applications.
Catalytic Asymmetric Synthesis of 3-Hydroxy-3-trifluoromethyl Benzofuranones via Tandem Friedel-Crafts/Lactonization Reaction
Ren, Hai,Wang, Pan,Wang, Lijia,Tang, Yong
, p. 4886 - 4889 (2015)
A highly enantioselective and regioselective chiral Lewis acid catalyzed tandem Friedel-Crafts/lactonization reaction is reported, providing direct access to plenty of 3-hydroxy-3-trifluoromethyl benzofuran-2-ones in up to 94% yields with up to >99% ee. Mechanistic study reveals that the interactions between the phenolic hydroxyl group and trifluoropyruvate are the most likely contributing factor to the high enantio- and regioselectivity. Optically pure (-)-BHFF can be obtained in gram-scale with 0.05 mol % catalyst, demonstrating the potentially utility of this method in medicinal chemistry.
Catalytic Friedel-Crafts/lactonization domino reaction: Facile access to 3-Hydroxybenzofuran-2-one scaffold
Vetica, Fabrizio,Pelosi, Alessandra,Gambacorta, Augusto,Loreto, M. Antonietta,Miceli, Martina,Gasperi, Tecla
, p. 1899 - 1906 (2014/04/03)
A valuable Lewis-acid-catalysed domino reaction involving a Friedel-Crafts alkylation of variously substituted phenols followed by a direct lactonization has been successfully developed (22 examples, yields up to 98 %). This protocol tolerates not only op
Catalytic Friedel-Crafts/Lactonization Domino Reaction: Facile Access to 3-Hydroxybenzofuran-2-one Scaffold
Vetica, Fabrizio,Pelosi, Alessandra,Gambacorta, Augusto,Loreto, M. Antonietta,Miceli, Martina,Gasperi, Tecla
, p. 1899 - 1906 (2015/10/05)
A valuable Lewis-acid-catalysed domino reaction involving a Friedel-Crafts alkylation of variously substituted phenols followed by a direct lactonization has been successfully developed (22 examples, yields up to 98 %). This protocol tolerates not only op
Efficient one-pot synthesis of the GABAB positive allosteric modulator (R,S)-5,7-Di-tert-butyl-3-hydroxy-3-trifluoromethyl-3H-benzofuran-2- one
Alker, Andre M.,Grillet, Francois,Malherbe, Pari,Norcross, Roger D.,Thomas, Andrew W.,Masciadri, Raffaello
, p. 3398 - 3405 (2008/12/23)
The GABAB positive allosteric modulator (R,S)-5,7-di-tert-butyl- 3-hydroxy-3-trifluoromethyl-3H-benzofuran-2-one (1) was synthesized in one pot from the anhydrous lithium salt of 2,4-di-tert-butylphenol and methyl trifluoropyruvate mediated by a stoichiometric amount of anhydrous gallium(III) chloride in 64% overall yield. The enantiomers of 1 were separated by chiral-phase HPLC (Chiralpak AD), and the absolute configuration was determined by X-ray crystallography. Copyright Taylor & Francis Group, LLC.
2-phenyl-3,3,3-trifluoro-2-hydroxy-propionic acid derivatives
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Page/Page column 8, (2008/06/13)
The present invention relates to compounds of formula I: wherein R1, R2, R3, R4, R5 and R6 are as defined in the specification and claims, which compounds are active on the GABAB /sub
