Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements

Port, Adriana; Virgili, Albert; Alvarez-Larena, A.; Piniella, J. F.

doi:10.1016/s0957-4166(00)00334-7

Cited by 30 publications

(10 citation statements)

References 24 publications

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“…Donor-acceptor CSAs incorporate sites for hydrogen bonding or other dipoledipole interactions, either electron-rich or -deficient aromatic rings forinteractions, or groups that may sterically hinder association of one configuration of a pair of enantiomers. 104 The increased steric effects of the tert-butyl group enhanced the discrimination compared to the corresponding 1-(1-naphthyl)ethylamine. 98 Figure 13 shows how such reagents can be used to discriminate chiral sulfoxides and lactones, and is quite similar to the mechanism of discrimination with Mosher's reagent.…”

Section: Donor-acceptor Systemsmentioning

confidence: 99%

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

2003

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Section: Donor-acceptor Systemsmentioning

confidence: 99%

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

2003

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“…Examples are the addition of cyclopropyllithium compounds to cyclopropanecarbonitriles, [47] the addition of organolithium reagents to aziridine-2-carbonitriles, [48] the reaction of phenyllithium with cyclopropanecarbonitrile (see Scheme 5), [49] and the addition of 1-naphthyllithium to pivalonitrile. [50] The anion obtained by deprotonation of 6-methyl-2,3,4,5-tetrahydropyridine (9) with lithium diisopropylamide can be reacted with hexanenitrile and results, after aqueous workup, in the formation of the 4-amino-1-azabuta-1,3-diene. [51] The latter reaction was applied in a multistep synthesis of N-bridgehead pyrroles 10 by addition of the lithium azaenolate of 6-methyl-2,3,4,5-tetrahydropyridine to a nitrile, carbanion trapping with propargyl bromide, and cycloamination (Scheme 6).…”

Section: Methods 5: From Nitrilesmentioning

confidence: 99%

Product Class 7: Imines

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Compounds with the general structure R 1 R 2 C=NR 3 , referred to as imines, were first obtained by Schiff via condensation of ketones and aldehydes with primary amines. Therefore, the condensation products are also called Schiff bases. In addition, the nominations azomethine, ketimine (derived from ketones), aldimine (derived from aldehydes), and anil (derived from anilines) are in use. It is recommended that the terms imine(s), ketimine(s), or aldimine(s) are used, rather than Schiff base(s) or azomethine(s).Since imines have to be considered as analogues of carbonyl compounds, many of the chemical properties are similar to the latter. Imines are used in new C-C bond formations, and reactions with electrophiles (e.g., aldehydes, alkyl halides), and the C=N moiety can undergo nucleophilic reactions. Generally, imines are very useful compounds in organic synthesis, as they are used in several syntheses of aza-heterocyclic compounds. Most imines are stable in an alkaline medium and therefore can be dried over potassium hydroxide. In diluted acid, however, they are easily hydrolyzed. In many cases intermediary imines cannot be isolated because of their lability. The presence of a C=N bond creates the possibility for E/Z isomerism (syn/anti). It has been recognized that such geomet-

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“…The investigation of the chiral recognition of carboxylic acids by artificial receptors was of critical importance in the preparation, separation, and analysis of enantiomerically pure carboxylic acids and disclosing the mechanism of interaction of the carboxylic acids with biological systems. Therefore, a variety of chiral shift reagents, such as chiral amines,19–24 amino alcohols,25 Tröger's Base,26 macrocyclic amines and amides,27–34 crown ethers,35–37 and calixarenes,38–43 have been described in the literature to determine the enantiomeric purity and understand the basis of the mechanism of host–guest complexations. To date, however, there are only a few examples of proline‐derived receptors44, 45 for the enantiomeric recognition of carboxylic acids.…”

Section: Introductionmentioning

confidence: 99%

Application of L‐proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids

Naziroglu¹,

Durmaz²,

Bozkurt³

et al. 2011

Chirality

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Four proline-derived chiral receptors 5-8 were readily synthesized starting from L-proline. The enantiomeric recognition ability of chiral receptors was examined with a series of carboxylic acids by (1) H NMR spectroscopy. The molar ratio and the association constants of the chiral compounds with each of the enantiomers of guest molecules were determined by using Job plots and a nonlinear least-squares fitting method, respectively. The Job plots indicate that the hosts form 1:1 instantaneous complexes with all guests. The receptors exhibited different chiral recognition abilities toward the enantiomers of racemic guests. Among the chiral receptors used in this study, prolinamide 6 was found to be the best chiral shift reagent and is effective for the determination of the enantiomeric excess of chiral carboxylic acids.

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Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements

Cited by 30 publications

References 24 publications

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy

Product Class 7: Imines

Application of L‐proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids

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