Reversible Enantiofacial Differentiation of a Single Heterocyclic Substrate by Supramolecular Receptors

Schopohl, Matthias C.; Siering, Carsten; Kataeva, О. N.; Waldvogel, Siegfried R.

doi:10.1002/anie.200351102

Cited by 41 publications

(25 citation statements)

References 14 publications

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“…The novel concept for the enantiofacial differentiation of caffeine molecules by supramolecular interactions were first proposed by Waldvogel [161]. He suggested two enantiofacial isomers a-and b-forms of caffeine (Fig.…”

Section: Molecular Recognition Of Caffeine With Polyphenols and Carbomentioning

confidence: 99%

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Molecular recognition of caffeine in solution and solid state

Sahoo

2015

Bioorganic Chemistry

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Section: Molecular Recognition Of Caffeine With Polyphenols and Carbomentioning

confidence: 99%

“…Enantiofacial isomers a-and b-forms of caffeine, first proposed by Waldvogel[161].The repulsive interactions of two different isomers can be achieved by steric modifications of the cavity of the receptor.…”

mentioning

confidence: 99%

Molecular recognition of caffeine in solution and solid state

Sahoo

2015

Bioorganic Chemistry

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“…The use of triphenylenes in discotic liquid crystals [1–2] as building blocks in supramolecular chemistry [3–4] as well as in solid-state chemistry [5] is well documented. Furthermore, triphenylenes are applied as components of functional polymers [6–7] and fluorescent labels [8–9].…”

Section: Introductionmentioning

confidence: 99%

Efficient electroorganic synthesis of 2,3,6,7,10,11-hexahydroxytriphenylene derivatives

Regenbrecht¹,

Waldvogel²

2012

Beilstein J. Org. Chem.

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Summary2,3,6,7,10,11-Hexahydroxytriphenylene of good quality and purity can be obtained via anodic treatment of catechol ketals and subsequent acidic hydrolysis. The electrolysis is conducted in propylene carbonate circumventing toxic and expensive acetonitrile. The protocol is simple to perform and superior to other chemical or electrochemical methods. The key of the method is based on the low solubility of the anodically trimerized product. The shift of potentials is supported by cyclic voltammetry studies.

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“…The binding is often based on electrostatic interactions, while only a few cases involve the binding of a neutral guest 13. Before our initial reports there was no supramolecular approach for enantiofacial discrimination on a prochiral aromatic compound as a whole 14…”

Section: Introductionmentioning

confidence: 99%

Direct Assignment of Enantiofacial Discrimination on Single Heterocyclic Substrates by Self‐induced CD

Siering

Grimme

Waldvogel

2005

Chemistry A European J

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The first direct assignment of highly dynamic enantiofacial discrimination acting on a single heterocyclic substrate has been achieved by a combination of experimental and theoretical CD spectroscopy. The interaction of chirally modified hosts based on triphenylene ketals with appropriate prochiral guests can lead to the preferential formation of one diastereomeric host-guest complex. This reversible stereoselective binding transmits the chiral information from remote chiral groups in the host to the strongly absorbing triphenylene chromophore, which gives rise to self-induced CD. This effect was exploited for the determination of the enantiofacial recognition in various host-guest systems. Inversion of the steric demand either of the chiral substituents at the host or of the prochiral guest leads to almost complete inversion of the resulting CD spectra. For the assignment of the absolute stereochemistry of the complexes, a combined molecular dynamics/quantum-chemical approach was successfully employed. Despite the size and the highly dynamic character of the supramolecular systems, fundamental properties of the systems and details of the spectra were simulated accurately, providing access to fast and reliable assignment of the enantiofacial preference. The results are highly consistent with available X-ray data.

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Reversible Enantiofacial Differentiation of a Single Heterocyclic Substrate by Supramolecular Receptors

Cited by 41 publications

References 14 publications

Molecular recognition of caffeine in solution and solid state

Molecular recognition of caffeine in solution and solid state

Efficient electroorganic synthesis of 2,3,6,7,10,11-hexahydroxytriphenylene derivatives

Direct Assignment of Enantiofacial Discrimination on Single Heterocyclic Substrates by Self‐induced CD

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