Calix[4]arene, calix[4]resorcarene, and cyclodextrin derivatives and their lanthanide complexes as chiral NMR shift reagents

Chirality

Volumn 15, Issue SUPPL., 2003, Pages

  Smith, Kristin J ^a   Wilcox, James D ^a   Mirick, Gudrun E ^a   Wacker, Lee S ^a   Ryan, Nicole S ^a   Vensel, David A ^a   Readling, Regina ^a   Domush, Hilary L ^a   Amonoo, Edwin P ^a   Shariff, Sonia S ^a   Wenzel, Thomas J ^a  

^a BATES COLLEGE   (United States)

Author keywords

Calixarenes, calixresorcarenes, cyclodextrins, enantiomeric excess; Chiral shift reagents; Lanthanide shift reagents, chiral solvating agents; NMR

Indexed keywords

AMINE; AMINO ACID; BETA CYCLODEXTRIN DERIVATIVE; CALIX[4]ARENE; CALIX[4]RESORCARENE; CALIXARENE; CARBINOXAMINE; CHIRAL SHIFT REAGENT; CHIRAL SOLVENT; CHLOROFORM; CYCLODEXTRIN; CYCLODEXTRIN DERIVATIVE; DOXYLAMINE; HYDROXYL GROUP; LANTHANIDE; LANTHANIDE COMPLEX; LANTHANIDE SHIFT REAGENT; METHANOL; PHENIRAMINE; PHENOL; REAGENT; SOLVENT; UNCLASSIFIED DRUG; WATER;

CHIRALITY; CONFERENCE PAPER; ENANTIOMER; ENANTIOMERIC EXCESS; IMAGE ENHANCEMENT; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CALIXARENES; CATECHOLS; CATIONS; CYCLODEXTRINS; HYDROLYSIS; LANTHANOID SERIES ELEMENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PHENOLS; POLYMERS; STEREOISOMERISM; TEMPERATURE;

EID: 10744222472     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10254     Document Type: Conference Paper

References (35)

1. Wenzel TJ, Wilcox JD. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality, 2003;15:256-270.
2. Webb TH, Wilcox CS. Enantioselective and diastereoselective molecular recognition of neutral molecules. Chem Soc Rev 1993:383-395.
3. Parker D. NMR determination of enantiomeric purity. Chem Rev 1991; 91:1441-1457.
4. Wenzel TJ. Magnetic resonance: enantiomeric purity studies using NMR. Encyclopedia of spectroscopy and spectrometry. New York: Academic Press; 2000;1:411-421.
5. Pirkle WH, Sikkenga DL. Use of achiral shift reagents to indicate relative stabilities of diastereomeric solvates. J Org Chem 1975;40: 3430-3434.
6. Pirkle WH, Sikkenga DL, Pavlin MS. Nuclear magnetic resonance determination of enantiomeric composition and absolute configuration of γ-lactones using chiral 2,2,2-trifluoro-1-(9-anthryl)ethanol. J Org Chem 1977;42:384-387.
7. Wenzel TJ, Morin CA, Brechting AA. Lanthanide-chiral resolving agent mixtures as chiral NMR shift reagents. J Org Chem 1992;57: 3594-3599.
8. Wenzel TJ, Miles RD, Weinstein SE. Chiral NMR shift reagents: lanthanide mixtures with 1-(1-naphthyl)ethylurea derivatives of amino acids. Chirality 1997;9:1-9.
9. Weinstein SE, Vining MS, Wenzel TJ. Lanthanide-crown ether mixtures as chiral NMR shift reagents for amino acid esters, amines, and amino alcohols. Magn Reson Chem 1997;35:273-280.
10. Wenzel TJ, Bogyo MS, Lebeau EL. Lanthanide-cyclodextrin complexes as probes for elucidating cyclodextrin-substrate interactions and optical purity by NMR spectroscopy. J Am Chem Soc 1994;116:4858-4865.
11. Wenzel TJ, Miles RD, Zomlefer K, Frederique DE, Roan MA, Troughton JS, Pond BV, Colby AL. Dysprosium (III)-diethylenetriaminepenta-acetate complexes of aminocyclodextrins as chiral NMR shift reagents. Chirality 2000;12:30-37.
12. Wenzel TJ, Thurston JE. (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid and its ytterbium(III) complex as chiral NMR discriminating agents. J Org Chem 2000;65:1243-1248.
13. Wenzel TJ, Thurston JE, Sek DC, Joly J-P. The utility of crown ethers derived from methyl β-D-galactopyranoside and their lanthanide couples as chiral NMR discriminating agents. Tetrahedron: Asymmetry 2001;12:1125-1130.
14. Wenzel TJ, Bean AC, Dunham SL. Chiral NMR shift reagents: mixtures of lanthanide tris(β-diketonates) with chiral carboxylate anions. Magn Reson Chem 1997;35:395-402.
15. Wenzel TJ, Brogan KL. Lanthanide-chiral carboxylate and chiral ester mixtures as NMR shift reagents. Enantiomer 2000;5:293-302.
16. Yanagihara R, Tominaga M, Aoyama Y. Chiral host-guest interaction. A water-soluble calix[4]resorcarene having L-proline moieties as a nonlanthanide chiral NMR shift reagent for chiral aromatic guests in water. J Org Chem 1994;59:6865-6867.
17. Ito K, Kida A, Ohba Y, Sone T. Syntheses of chiral calixarene analog incorporating amino acid residues: molecular recognition for a racemic ammonium ion by the macrocycles. Chem Lett 1998;1221-1222.
18. Saito S, Nuckolls C, Rebek J Jr. New molecular vessels: synthesis and chiroselective recognition. J Am Chem Soc 2000;122:9628-9630.
19. Gutsche CD. Calixarenes. Cambridge, UK: Royal Society of Chemistry; 1989:27-50.
20. Sternbach LN, Fryer RI, Metlesics W, Reeder E, Sach G, Saucy G, Stempel A. Quinazolines and 1,4-benzodiazepines. VI. Halo-, methyl-, and methoxy-substituted 1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-ones. J Org Chem 1962;27:3788-3796.
21. Chang SK, Cho I. New metal cation-selective ionophores derived from calixarenes: their syntheses and ion-binding properties. J Chem Soc Perkin 1 1986:211-214.
22. Pena MS, Zhang Y, Thibodeaux S, McLaughlin ML, de la Pena AM, Warner IM. Synthesis of a water-soluble chiral N-acylcalix(4)arene amino acid derivative. Tetrahedron Lett 1996;37:5841-5844.
23. Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ. Host-guest complexation. 48. Octol building blocks for cavitands and carcerands. J Org Chem 1989; 54:1305-1312.
24. Iwanek W, Mattay J. Chiral calixarenes derived from resorcinol. Liebigs Ann 1995:1463-1466.
25. Iwanek W. Chiral calixarene derived from resorcinol. 4. Diastereoselective closure of the oxazine ring. Tetrahedron: Asymmetry 1998; 9:4289-4290.
26. Pena MS, Zhang Y, Warner IM. Enantiomeric separations by use of calixarene electrokinetic chromatography. Anal Chem 1997;69:3239-3242.
27. Wenzel TJ. NMR Shift Reagents. Boca Raton, FL: CRC Press; 1987.
28. Matsushita Y, Matsui T. Synthesis of aminomethylated calix[4]resorcinarenes. Tetrahedron Lett 1993;34:7433-7436.
29. Arnecke R, Bohmer V, Friebe S, Gebauer S, Krauss GJ, Thondorf I, Vogt W. Regio- and diastereoselective condensation of resorcarenes with primary amines and formaldehyde. Tetrahedron Lett 1995;36: 6221-6224.
30. Iwanek W, Urbaniak M. Chiral calixarenes derived from resorcinol. 6. Chiral discrimination by resorcarenes. Pol J Chem 1999;73:2067-2072.
31. Kean SD, Easton CJ, Lincoln SF, Parker D. A preparative and solution study of a modified β-cyclodextrin and its europium(III) complex, and their interactions with racemic amino acid anions. Aust J Chem 2001; 54:535-539.
32. Fillet M, Crommen PhHJ. Enantiomeric separations of drugs using mixtures of charged and neutral cyclodextrins. J Chromatogr A 2000; 875:123-134.
33. Owens PK, Fell AF, Coleman MW, Berridge JC. Screening of cyclodextrins by nuclear magnetic resonance for the design of chiral capillary electrophoresis separations. J Chromatogr A 1998;797:149-164.
34. Hellreigel C, Handel H, Wedig M, Steinhauer S, Sorgel F, Albert K, Holzgrabe U. Study on the chiral recognition of the enantiomers of ephidrine derivatives with neutral and sulfated heptakis(2,3-O-diacetyl)-β-cyclodextrins using capillary electrophoresis, UV, nuclear magnetic resonance spectroscopy and mass spectrometry. J Chromatogr A 2001;914:315-324.
35. Chankvetadze B, Schulte G, Bergenthal D, Blaschke G. Comparative capillary electrophoresis and NMR studies of enantioseparation of dimethindene with cyclodextrins. J Chromatogr A 1998;798:315-323.