The solid state and solution conformational behaviour of a chiral 30-crown-10 derivative synthesised from 1,4:3,6-dianhydro-D-mannitol; X-ray crystal structure

Metcalfe, Janet C.; Jones, Geraint; Crawshaw, T. H.; Quick, Andrew; Williams, David J.

doi:10.1039/c39810000430

Cited by 15 publications

(8 citation statements)

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“…For example, a crown ether that contains two isomannide units has been prepared, and its properties in metal-ion complexation have been analyzed (Figure 2 a). [45] Reetz et al have reported isomannidebased diphosphite ligands, which have been successfully applied as bidentate ligands for rhodium species in the asymmetric hydrogenation of dimethyl itaconate with an exceptionally high enantioselectivity. [46] In a similar approach demonstrated by Bakos et al, isomannide was converted via the ditosylated intermediate through Walden inversion of the C-2 and C-5 configuration exclusively to 1,4:3,6-dianhydro-2,5-dideoxy-2,5-bis-(diphenylphosphino)-l-iditol.…”

Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

“…Syntheses of 1,4:2,5:3,6-trianhydro-and 2,5-amino-1,4:3,6-dianhydro-d-mannitol via the ditosylated derivatives of isosorbide and isoidide using a) sodium ethoxide and b) methanolic ammonia. [41,42] Figure 2. a) Isomannide-based crown ether [45] and b) an isosorbide-based chiral auxiliary. [51a] carboxylic acids has been investigated, for example, by using dichloromethane as the solvent and 4-dimethylaminopyridine as the catalyst.…”

Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

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Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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Isosorbide is a platform chemical of considerable importance for the future replacement of fossil resource-based products. Applications as monomers and building blocks for new polymers and functional materials, new organic solvents, for medical and pharmaceutical applications, and even as fuels or fuel additives are conceivable. The conversion of isosorbide to valuable derivatives by functionalization or substitution of the hydroxyl groups is difficult because of the different configurations of the 2- and 5-positions and the resulting different reactivity and steric hindrance of the two hydroxyl groups. Although a substantial amount of work has been published using exclusively the endo or exo derivatives isomannide and isoidide, respectively, as starting material, a considerable effort is still necessary to transfer and adapt these methods for the efficient conversion of isosorbide. This Minireview deals with all aspects of isosorbide chemistry, which includes its production by catalytic processes, special properties, and chemical transformations for its utilization in biogenic polymers and other applications of interest.

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Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

Section: Chiral Auxiliaries and Other Chemicalsmentioning

confidence: 99%

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

2011

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“…Crown ether type receptors and [2]catenanes based on the isomannide skeleton have been reported [14].…”

Section: Design and Synthesis Of Tectonsmentioning

confidence: 99%

Molecular tectonics: design and structural analysis of enantiomerically pure tectons and helical coordination networks

Grosshans¹,

Jouaiti²,

Bulach³

et al. 2004

Comptes Rendus. Chimie

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“…'H N.m.r. spectra (220 MHz) of complexes of diaza-crown ethers (6), (7), and (11) with primary alkylammonium thiocyanates" and diazacrown ether (1 1) with hydronium thiocyanate…”

Section: Diaza-crownmentioning

confidence: 99%

“…'3-'5'16 Thi s suggests that all of the macrocycle heteroatoms are involved in binding the two guest cations but, in the absence of more precise structural information, it is not possible to speculate on the distribution of the hydrogen bonding that is involved. The 2: 1 complex between methylammonium thiocyanate and the diaza-24-crown-8 (7) gives an n.m.r. spectrum that is less well resolved but spectral changes below -100 "C are not inconsistent with the formation of a complex analogous to (17a).…”

Section: Host Spectrummentioning

confidence: 99%

Formation of complexes between aza derivatives of crown ethers and primary alkylammonium salts. Part 8. 12-Crown-4, 15-crown-5, 21-crown-7, and 24-crown-8 derivatives

Johnson¹,

Jones²,

Sutherland³

et al. 1985

J. Chem. Soc., Perkin Trans. 1

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The monoaza-crown ethers (3), (4), and (5) and the diaza-crown ethers (6), ( 7), (lo), and (11) form complexes with primary alkylammonium thiocyanates in organic solvents. The diaza-15-crown-5 system (11) forms well defined 1 : 1 complexes with the cis-,cis-stereochemistry shown in ( 16) but the diaza-24-crown-8 derivative (7) forms a 2 : 1 complex (G : H ratio) with benzylammonium thiocyanate having the cis,cis,trans,trans-stereochemistry (1 7a). The diaza-24-crown-6 derivative (1 0) forms weak 1 : 1 complexes which apparently adopt the double nesting conformation (18).

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The solid state and solution conformational behaviour of a chiral 30-crown-10 derivative synthesised from 1,4:3,6-dianhydro-D-mannitol; X-ray crystal structure

Cited by 15 publications

References 0 publications

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

Isosorbide as a Renewable Platform chemical for Versatile Applications—Quo Vadis?

Molecular tectonics: design and structural analysis of enantiomerically pure tectons and helical coordination networks

Formation of complexes between aza derivatives of crown ethers and primary alkylammonium salts. Part 8. 12-Crown-4, 15-crown-5, 21-crown-7, and 24-crown-8 derivatives

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