Chiral Recognition of Aminoalcohols by1H and13C NMR Spectroscopy using binaphthyl derivatives as chiral solvating agents

Koy, Cornelia; Michalik, Manfred; Döbler, Christian; Oehme, G.

doi:10.1002/prac.199733901119

Cited by 11 publications

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“…Despite experimental difficulties, other amino alcohols of the norbornane series, in particular 75-79 were obtained, and many of them were isolated as optically active substances. Their optical purity was determined by 1 H and 13 C NMR spectroscopy using (+)-1,1′-binaphthalene-2,2′-diol and its derivatives [78,79].…”

Section: Nhrmentioning

confidence: 99%

Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

Пальчиков

2010

Russ J Org Chem

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The review analyzes methods for the synthesis of amino alcohols containing cage-like norbornene, norbornane, and adamantane fragments. Such reactions of amino alcohols as selective functionalization of hydroxy and amino groups, as well as heterocyclizations with formation of nitrogen-and oxygen-containing heterocycles, are considered. Biological activity of cage-like amino alcohols and their derivatives and their use as ligands in catalytic asymmetric syntheses are discussed.

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Section: Nhrmentioning

confidence: 99%

Cage-like amino alcohols. synthesis, reactions, and application

Kas’yan

Пальчиков

2010

Russ J Org Chem

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“…It has to be considered that, though the lack of signal multiplicity is an advantage for overcoming overlapping and for the integration of enantiodifferentiated signals, it also means a loss of molecular structural information which is valuable for the assignment of the individual peaks (especially when working with mixtures). To date, just very few studies using CSA have explored the use of 13 C NMR spectroscopy. − We believe that the reason of that disuse resides in the intrinsic low sensitivity of 13 C compared to 1 H (low natural abundance, 1.1%, and a gyromagnetic ratio 1/4 smaller than that of the 1 H).…”

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confidence: 99%

¹³C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents

2013

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The utility of (13)C NMR spectroscopy for the differentiation of enantiomers using chiral solvating agents (CSA) is stated. Three examples involving the enantiodifferentiation of a drug, a metabolite and a reactant in aqueous and organic solutions have been chosen to show it. The intrinsic high dispersion of (13)C nucleus, as well as the singlet nature of the signals in standard experiments makes (13)C NMR experiments a powerful alternative or complement to (1)H NMR experiments; specially, when studying pure compounds with complex proton spectra or mixtures of compounds, as in chiral metabonomics, where severe overlapping exists in proton spectrum. To evaluate and compare the quality of the enantioresolution of a NMR signal we introduce the enantiodifferentiation quotient, E, that considers the complexity of (1)H multiplets (and in general the width) of the original signal. It has been observed that the error in the measurement of the enantiomeric molar ratio can be related to the E value. The sensitivity and experimental time of a wide range of chiral analyte concentrations were also assessed.

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ChemInform Abstract: Chiral Recognition of Amino Alcohols by ¹H and ¹³C NMR Spectroscopy Using Binaphthyl Derivatives as Chiral Solvating Agents.

et al. 1998

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stereochemistry stereochemistry (general, optical resolution) O 0030 -019Chiral Recognition of Amino Alcohols by 1 H and 13 C NMR Spectroscopy Using Binaphthyl Derivatives as Chiral Solvating Agents.-Different signals in the spectra are doubled in dependence on the substrate as well as the agent. In the 1 H NMR spectra mainly the CH 3 N signal is a useful indicator in observing the effect of chiral discrimination. Only in case of (I) remarkable splittings for H-1 and H-2 are observed. The largest shift differences shows the host-guest pair (±)-(I)/(+)-(VIa). The splittings found in (II) and (III) are essentially smaller. Only low shift differences are observed for the non-cyclic compound (V). -(KOY, C.; MICHALIK, M.; DOEBLER, C.; OEHME, G.; J. Prakt. Chem./Chem.

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Chiral Recognition of Aminoalcohols by1H and13C NMR Spectroscopy using binaphthyl derivatives as chiral solvating agents

Cited by 11 publications

References 20 publications

Cage-like amino alcohols. synthesis, reactions, and application

Cage-like amino alcohols. synthesis, reactions, and application

¹³C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents

ChemInform Abstract: Chiral Recognition of Amino Alcohols by ¹H and ¹³C NMR Spectroscopy Using Binaphthyl Derivatives as Chiral Solvating Agents.

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Chiral Recognition of Aminoalcohols by1H and13C NMR Spectroscopy using binaphthyl derivatives as chiral solvating agents

Cited by 11 publications

References 20 publications

Cage-like amino alcohols. synthesis, reactions, and application

Cage-like amino alcohols. synthesis, reactions, and application

13C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents

ChemInform Abstract: Chiral Recognition of Amino Alcohols by 1H and 13C NMR Spectroscopy Using Binaphthyl Derivatives as Chiral Solvating Agents.

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Product

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¹³C NMR Spectroscopy for the Differentiation of Enantiomers Using Chiral Solvating Agents

ChemInform Abstract: Chiral Recognition of Amino Alcohols by ¹H and ¹³C NMR Spectroscopy Using Binaphthyl Derivatives as Chiral Solvating Agents.