Enantiomeric Resolution of Cycloenantiomeric Rotaxane, Topologically Chiral Catenane, and Pretzel-Shaped Molecules:  Observation of Pronounced Circular Dichroism

Yamamoto, Chiyo; Okamoto, Yoshio; Schmidt, Thomas; Jäger, and Ralf; Vögtle, Fritz

doi:10.1021/ja971764q

Cited by 175 publications

(74 citation statements)

References 25 publications

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“…Since there were no observable diastereomers due to the above-mentioned reasons and this type of chiral HPLCcolumn has been used for catenane enantioseparation before, 8,13 we successfully separated the enantiomers using a Chiralcel-OD column. 13 It proceeded with a clear baseline separation but the separation factor (␣ = 2.39) was some- how lower than that of the catenane 9c (␣ = 2.68).…”

Section: Resultsmentioning

confidence: 99%

Regioselective template synthesis, X-ray structure, and chiroptical properties of a topologically chiral sulfonamide catenane

et al. 2000

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Section: Resultsmentioning

confidence: 99%

Regioselective template synthesis, X-ray structure, and chiroptical properties of a topologically chiral sulfonamide catenane

et al. 2000

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“…[54] We, in turn, have been successful in effecting the chiral resolution of topologically chiral catenanes, pretzelanes, [55] and a cyclodiastereoisomeric [3]rotaxane [56] of the amide type by using HPLC columns with chiral stationary phases. Our initial efforts towards enantioseparation of amide-knotanes were focused on finding an appropriate HPLC chiral stationary phase.…”

Section: Chiral Resolution Absolute Configuration and Chiral Inductmentioning

confidence: 99%

Knotting and Threading of Molecules: Chemistry and Chirality of Molecular Knots and Their Assemblies

2005

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How and why do molecules tangle or thread? Investigations of molecular knots (knotanes) may shed some light on the mechanisms of (supra)molecular templation and the folding of molecules that result in intertwining. The topological chirality of these fascinating molecules leads to new types of isomerism and paves the way to nanosized molecular motors. Their preparation and derivatization makes high demands on modern synthetic methods and analytical separation since molecular knots are formed in a more or less planned design based on metal coordination or hydrogen-bonding patterns. This Review describes the development of templation techniques for the synthesis of knotanes and their chiral resolution as well as their selective functionalization and use as building blocks in the synthesis of higher knotane assemblies. Such assemblies can possess linear, branched, or even macrocyclic structures which, on the one hand, introduce unprecedented isomeric compositions that arise from multiple topological stereogenic units and, on the other, define new types of artificial macromolecules beyond polymers and dendritic species.

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“…[5] The observation of axial chirality (sometimes referred to as cyclochirality) was first noted by Prelog in connection with cyclopeptides, [6] and has subsequently been studied in a number of other areas, including rotaxanes. [7] Cyclochirality, as applied to resorcinarenes, has been discussed in several recent reviews.…”

Section: Introductionmentioning

confidence: 99%

The Diastereoselective Formation of Tetraalkoxy[4]resorcinarenes Derived from (–)‐(2R)‐2‐Methoxy‐2‐phenylethanol and Proof of Absolute Configurations

et al. 2011

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The preparation of optically pure (-)-3-[(2R)-2-methoxy-2-phenylethoxy] phenol from resorcinol monobenzoate and its conversion into diastereoisomeric tetraalkoxyresorcin[4]arenes together with proof of the absolute configurations of the products is reported. The results of the study indicate that diastereoselective ring closure of linear tetrameric intermediates is controlled by the steric demand of the alkyl group in the precursor 3-alkoxyphenol

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Enantiomeric Resolution of Cycloenantiomeric Rotaxane, Topologically Chiral Catenane, and Pretzel-Shaped Molecules: Observation of Pronounced Circular Dichroism

Cited by 175 publications

References 25 publications

Regioselective template synthesis, X-ray structure, and chiroptical properties of a topologically chiral sulfonamide catenane

Regioselective template synthesis, X-ray structure, and chiroptical properties of a topologically chiral sulfonamide catenane

Knotting and Threading of Molecules: Chemistry and Chirality of Molecular Knots and Their Assemblies

The Diastereoselective Formation of Tetraalkoxy[4]resorcinarenes Derived from (–)‐(2R)‐2‐Methoxy‐2‐phenylethanol and Proof of Absolute Configurations

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