¹³C NMR differentiation of diastereoisomeric complexes of cis-decalin with β-cyclodextrin

Abstract

13C NMR spectra show chiral discrimination between t w o invertomers of cis-decalin complexed with (J-cyclodextrin.

Carboxymethylated cyclodextrin derivatives as chiral NMR discriminating agents

“…[1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] Subsequent work showed that the small degree of enantiomeric discrimination, that is often observed in the spectrum of substrates in the presence of cyclodextrins, can be enhanced by coupling a paramagnetic lanthanide ion to the system. [21][22][23] Covalent attachment of a diethylenetriaminepentaacetic acid moiety to the cyclodextrin through an amide bond provided the lanthanide binding site.…”

Water‐soluble calix[4]resorcinarenes as chiral NMR solvating agents for bicyclic aromatic compounds

“…The interior of the cavity is often hydrophobic, such that the hydrophobic portion of organic salts is stabilized by insertion into the cavity in water. Native cyclodextrins, [14][15][16][17][18] trimethyl-b-cyclodextrin, [19][20][21][22][23] and carboxymethylated cyclodextrins [24][25][26][27][28][29] are one family of water-soluble cavity compounds. The crown ether (18-crown-6)-2,3,11,12-tetracarboxylic acid has been used in water as a chiral solvating agent for primary amines, 30 although the enantiomeric discrimination with this crown ether is better in methanol and acetonitrile.…”

Water‐Soluble Calix[4]resorcinarenes with Hydroxyproline Groups as Chiral NMR Solvating Agents for Phenyl‐ and Pyridyl‐Containing Compounds

“…These compounds have a range of functional groups in the substituent attached to the phenyl ring and include series of compounds with methylbenzylamine (6-10) and benzyl alcohol (11)(12)(13)(14)(15) units. Compounds 6 and 13-15 have been previously studied with these calix [4]resorcinarenes, and certain data is included herein for comparative purposes.…”

“…Water-soluble chiral NMR solvating agents are far less common. The most widely studied and broadly applicable water-soluble chiral NMR shift reagents include native cyclodextrins [7][8][9][10][11] and certain water-soluble cyclodextrin derivatives. [12][13][14][15][16][17][18][19][20][21][22][23][24] Given the growing emphasis on the use of water as a green solvent in synthetic chemistry and the importance of water solubility for pharmaceuticals, there is a need for additional watersoluble chiral NMR shift reagents.…”