Synthesis and characterization of fluorous (S)- and (R)-1-phenylethylamines that effect heat facilitated resolution of (±)-2-(8-carboxy-1-naphthylsulfinyl)benzoic acid via diastereomeric salt formation and study of their circular dichroism

Szabó, Dénes; Nemes, Anikó; Kövesdi, István; Farkas, Viktor; Hollósi, Miklós; Rábai, József

doi:10.1016/j.jfluchem.2006.05.011

Cited by 7 publications

(1 citation statement)

References 35 publications

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“…Synthesis and utilization of nonafluoro- tert -butoxy group-containing chiral molecules are still limited. − Previously, we reported the synthesis of three α-(nonafluoro- tert -butoxy)carboxylic acids, two of which are in the optically active form [( R )- 1 , ( RS )- 2 , ( R )- 3 ] (Figure ) …”

Section: Introductionmentioning

confidence: 99%

Chiral Recognition Studies of α-(Nonafluoro-tert-butoxy)carboxylic Acids by NMR Spectroscopy

et al. 2015

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Three chiral α-(nonafluoro-tert-butoxy)carboxylic acids (R)-1, (RS)-2, (R)-3 were synthesized to examine their application as chiral solvating agents with amines. As a model compound, first (S)- and/or (RS)-α-phenylethylamine was used, and their diastereomeric salts were investigated by (1)H and (19)F NMR and ECD spectroscopy. The NMR spectroscopic studies were carried out at room temperature using the slightly polar CDCl3 and apolar C6D6 as solvents in 5 mM and 54 mM concentrations. The difference of the chemical shifts (Δδ) in the diastereomeric complexes is comparable with other, well-known chiral derivatizing and solvating agents (e.g., Mosher's acid, Pirkle's alcohol). Diastereomeric salts of racemic acids (RS)-1 and (RS)-2 with biologically active amines (1R,2S)-ephedrine and (S)-dapoxetine were also investigated by (19)F NMR spectroscopy.

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Section: Introductionmentioning

confidence: 99%

Chiral Recognition Studies of α-(Nonafluoro-tert-butoxy)carboxylic Acids by NMR Spectroscopy

et al. 2015

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Synthesis and Characterization of Fluorous (S)‐ and (R)‐1‐Phenylethylamines that Effect Heat Facilitated Resolution of (.+‐.)‐2‐(8‐Carboxy‐1‐naphthylsulfinyl)benzoic Acid via Diasteromeric Salt Formation and Study of Their Circular Dichroism.

et al. 2007

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Stereochemistry O 0030 Synthesis and Characterization of Fluorous (S)-and (R)-1-Phenylethylamines that Effect Heat Facilitated Resolution of (±)-2-(8-Carboxy-1-naphthylsulfinyl)benzoic Acid via Diasteromeric Salt Formation and Study of Their CircularDichroism. -(SZABO, D.; NEMES, A.; KOEVESDI, I.; FARKAS, V.; HOLLOSI, M.; RABAI*, J.; J. Fluorine Chem. 127 (2006) 10, 1405-1414; Inst. Chem., Eoetvoes Lorand Univ., H-1518 Budapest, Hung.; Eng.) -R. Staver 08-027

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Greener fluorous chemistry: Convenient preparation of new types of ‘CF3-rich’ secondary alkyl mesylates and their use for the synthesis of azides, amines, imidazoles and imidazolium salts

Nemes

Tölgyesi

Bodor

et al. 2010

Journal of Fluorine Chemistry

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Synthesis and characterization of fluorous (S)- and (R)-1-phenylethylamines that effect heat facilitated resolution of (±)-2-(8-carboxy-1-naphthylsulfinyl)benzoic acid via diastereomeric salt formation and study of their circular dichroism

Cited by 7 publications

References 35 publications

Chiral Recognition Studies of α-(Nonafluoro-tert-butoxy)carboxylic Acids by NMR Spectroscopy

Chiral Recognition Studies of α-(Nonafluoro-tert-butoxy)carboxylic Acids by NMR Spectroscopy

Synthesis and Characterization of Fluorous (S)‐ and (R)‐1‐Phenylethylamines that Effect Heat Facilitated Resolution of (.+‐.)‐2‐(8‐Carboxy‐1‐naphthylsulfinyl)benzoic Acid via Diasteromeric Salt Formation and Study of Their Circular Dichroism.

Greener fluorous chemistry: Convenient preparation of new types of ‘CF3-rich’ secondary alkyl mesylates and their use for the synthesis of azides, amines, imidazoles and imidazolium salts

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