Chiral NMR discrimination of amines: Analysis of secondary, tertiary, and prochiral amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid

Chirality

Volumn 20, Issue 3-4, 2008, Pages 370-378

  Lovely, Ann E ^a   Wenzel, Thomas J ^a  

^a BATES COLLEGE   (United States)

Author keywords

Chiral discrimination; Crown ethers; NMR; Prochiral amines; Secondary amines; Tertiary amines

Indexed keywords

AMINE; CARBOXYLIC ACID DERIVATIVE; CROWN COMPOUND;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HYDROGEN BOND; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

AMINES; CROWN ETHERS; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 39749202875     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20449     Document Type: Article

References (24)

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. Wenzel TJ. Enantiomeric purity studied using NMR. In: Trauter G, Holmes J, Lindon J, editors. Encyclopedia of spectroscopy, Vol. 1. New York: Academic Press; 2000. p 411-421.
3. Webb TH, Wilcox CS. Enantioselective and diastereoselective molecular recognition of neutral molecules. Chem Soc Rev 1993;22:383-395.
4. Parker D. NMR determination of enantiomeric purity. Chem Rev 1991;91:1441-1447.
5. Pirkle WH, Hoover DJ. NMR chiral solvating agents. In: Eliel EL, Wilen SH, editors. Top stereochem, Vol. 13. New York: Wiley Interscience; 1982. p 263-331.
6. Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117.
7. Sarfati M, Lesot P, Merlet D, Courtieu J. Theoretical and experimental aspects of enantiomeric differentiation using natural abundance multinuclear NMR spectroscopy in chiral polypeptide liquid crystals. Chem Commun 2000;2069-2081.
8. Schneider HJ, Hacket F, Rudiger V, Ikeda H. NMR studies of cyclodextrin and cyclodextrin complexes. Chem Rev 1998;98:1755-1786.
9. Helgeson RC, Timko JM, Moreau P, Peacock SC, Mayer JM, Cram DJ. Models for chiral recognition in molecular complexation. J Am Chem Soc 1974;96:6762-6763.
10. Stoddart JF. From carbohydrates to enzyme analogues. Chem Soc Rev 1979;8:85-142.
11. 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.
12. Wenzel TJ, Thurston JE. Enantiomeric discrimination in the NMR spectra of underivatized amino acids and α-methyl amino acids using (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Tetrahedron Lett 2000;41:3769-3772.
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, Freeman BE, Sek DC, Zopf JJ, Nakamura T, Yongzhu J, Hirose K, Tobe Y. Chiral recognition in NMR spectroscopy using crown ethers and their ytterbium(III) complexes. Anal Bioanal Chem 2004;378:1536-1547.
15. Machida Y, Kagawa M, Nishi H. Nuclear magnetic resonance studies for the chiral recognition of (+)-(R)-18-crown-6-tetracarboxylic acid to amino compounds. J Pharm Biomed Anal 2003;30.1929-1942.
16. Hirose K, Fujiwara A, Matsunaga K, Aoki N, Tobe Y. Chiral recognition of secondary amines by using chiral crown ether and podand. Tetrahedron Lett 2002;43:8539-8542.
17. Hirose K, Fujiwara A, Matsunaga K, Aoki N, Tobe Y. Preparation of phenolic crown ethers and podands and their enantiomer recognition ability toward secondary amines. Tetrahedron: Asymmetry 2003;14:555-566.
18. Sada K, Tateishi Y, Shinkai S. A chiral pybox ligand as a new chiral shift reagent for secondary dialkylammonium cations. Chem Lett 2004;33:582-583.
19. Suzuki T, Sada K, Tateishi Y, Tani T, Shinkai S. 2,6-Bis(benzoxazoyl)- pyridine (bzpybox) as a new dialkylammonium cation receptor. Tetrahedron Lett 2004;45:8161-8163.
20. Lovely AE, Wenzel TJ. Chiral NMR discrimination of secondary amines using (18-crown-6)-2,3,11,12-tetracarboxylic acid. Org Lett 2006;8:2823-2826.
21. Lovely AE, Wenzel TJ. Chiral NMR discrimination of pyrrolidines using (18-crown-6)-2,3,11,12-tetracarboxylic acid. Tetrahedron: Asymmetry 2006;17:2642-2648.
22. Lovely AE, Wenzel TJ. Chiral NMR discrimination of piperidines and piperazines using (18-crown-6)-2,3,11,12-tetracarboxylic acid. J Org Chem 2006;71:9178-9182.
23. Ogston AG. Interpretation of experiments on metabolic processes using isotopic tracer elements. Nature 1948;162:963.
24. Wenzel TJ. Discrimination of chiral compounds using NMR spectroscopy. Hoboken, New Jersey: Wiley Interscience; 2007.