α,α′-Bis(trifluoromethyl)-9,10-anthracenedimethanol: enantioselective synthesis and bidentate complexes with benzenedimethanols

Estivill, Carla; Ivanov, Petko M.; Pomares, Marta; Sánchez-Aris, M; Virgili, Albert

doi:10.1016/j.tetasy.2004.03.019

Cited by 7 publications

(2 citation statements)

References 28 publications

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“…(R,R)-a,a 0 -(bistrifluoromethyl)-9,10-Anthracenedimethanol (R,R-ABTE) was prepared in enantiopure form by the established procedure 19 and its enantiomeric purity (98 % e.e) was confirmed by analytical chiral HPLC. Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl phthalate (2), isophthalate (3) and terephthalate (4) were obtained in 19, 26, and 40% yields, respectively, by esterification of R,R-ABTE with phthalic, isophthalic, and terephthalic acid dichlorides Scheme 1 (An important improve of yield was experimentally observed if two equivalents of DCC were added).…”

Section: Results and Discussion Synthesis And Structural Analysismentioning

confidence: 99%

Molecular tweezers for enantiodiscrimination in NMR: Di‐(R,R)‐1‐[10‐(1‐hydroxy‐2,2,2‐trifluoroethyl)‐9‐anthryl]‐2,2,2‐trifluoroethyl benzenedicarboxylates

et al. 2009

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Section: Results and Discussion Synthesis And Structural Analysismentioning

confidence: 99%

Molecular tweezers for enantiodiscrimination in NMR: Di‐(R,R)‐1‐[10‐(1‐hydroxy‐2,2,2‐trifluoroethyl)‐9‐anthryl]‐2,2,2‐trifluoroethyl benzenedicarboxylates

et al. 2009

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“…R,R -ABTE was prepared in enantiopure form by the established procedure and its enantiomeric composition (98%) was confirmed by analytical chiral HPLC. Di-( R,R )-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthril]-2,2,2-trifluoroethyl muconate 2 was obtained in a 62% yield by esterifying R,R -ABTE with muconic acid at room temperature, in the presence of DCC and DMAP.…”

Section: Resultsmentioning

confidence: 99%

Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl Muconate: A Highly Chiral Cavity for Enantiodiscrimination by NMR

et al. 2006

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A new chiral molecular tweezer, di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl muconate 2, was synthesized in enantiopure form, and its geometry was studied using NMR and molecular mechanics. The effectiveness of 2 as a chiral solvating agent for determining the enantiomeric composition of chiral compounds using NMR was demonstrated, improving the results obtained with other methods. The stoichiometry and the association constant of the resulting diastereomeric complexes were studied, and their geometry was analyzed by NOE and 1H NMR.

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A New Chirally Organized Trifluoromethylanthrylmethanol Derivative and Its Application as Chiral Solvating Agent

et al. 2017

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The synthesis and structure of 1,1′‐(((10,10’‐(1,1′‐binaphthalene)‐2,2′‐diylbis(oxy))bis(methylene))bis(anthracene‐10,9‐diyl))bis(2,2,2‐trifluoroethanol), 4, is reported. This compound owns both axial and central chirality allowing its use as a chiral solvating agent (CSA) for the enantiomeric composition determination of several mixtures of chiral aromatic alcohols and amines using NMR. The study of the resulting diastereoisomeric complexes was carried out by determining its stoichiometry and association binding constants.

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α,α′-Bis(trifluoromethyl)-9,10-anthracenedimethanol: enantioselective synthesis and bidentate complexes with benzenedimethanols

Cited by 7 publications

References 28 publications

Molecular tweezers for enantiodiscrimination in NMR: Di‐(R,R)‐1‐[10‐(1‐hydroxy‐2,2,2‐trifluoroethyl)‐9‐anthryl]‐2,2,2‐trifluoroethyl benzenedicarboxylates

Molecular tweezers for enantiodiscrimination in NMR: Di‐(R,R)‐1‐[10‐(1‐hydroxy‐2,2,2‐trifluoroethyl)‐9‐anthryl]‐2,2,2‐trifluoroethyl benzenedicarboxylates

Di-(R,R)-1-[10-(1-hydroxy-2,2,2-trifluoroethyl)-9-anthryl]-2,2,2-trifluoroethyl Muconate: A Highly Chiral Cavity for Enantiodiscrimination by NMR

A New Chirally Organized Trifluoromethylanthrylmethanol Derivative and Its Application as Chiral Solvating Agent

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