High-performance liquid chromatographic enantioseparation of 1-(aminoalkyl)-2-naphthol analogs on polysaccharide-based chiral stationary phases

Chirality

Volumn 19, Issue 5, 2007, Pages 374-379

  Sztojkov Ivanov, Anita ^a   Tóth, Diana ^a   Szatmári, István ^a   Fülöp, Ferenc ^a   Péter, Antal ^b  

^a UNIVERSITY OF SZEGED   (Hungary)

^b UNIVERSITY OF SZEGED   (Hungary)

Author keywords

1 ( aminobenzyl) 2 naphthol; 1 (aminoalkyl) 2 naphthol analogs; Chiralcel OD H; Chiralcel OD RH; Enantioselective HPLC; Polysaccharide based chiral stationary phases

Indexed keywords

1 (ALPHA AMINOBENZYL) 2 NAPHTHOL DERIVATIVE; 2 NAPHTHOL; BUFFER; CELLULOSE; NAPHTHOL DERIVATIVE; PHOSPHATE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PH; PRIORITY JOURNAL; SEPARATION TECHNIQUE;

EID: 34247643109     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20392     Document Type: Article

References (30)

1. Betti M. α-Naphthol phenylaminomethane. Org Synth Colloid 1941; 1:381-383.
2. Szatmári I, Fülöp F. Synthesis and transformations of 1-(α-aminobenzyl)-2-naphthol derivatives. Curr Org Synth 2004;1:155-165.
3. Cardellichio C, Ciccarella G, Naso F, Schingaro E, Scordari F. The Betti base: absolute configuration and routes to a family of related chiral nonracemic bases. Tetrahedron: Asymmetry 1998;9:3667-3675.
4. Cardellicchio C, Ciccarella G, Naso F, Perna F, Tortorella P. Use of readily available chiral compounds related to the Betti base in the enantioselective addition of diethylzinc to aryl aldehydes. Tetrahedron 1999;55:14685-14692.
5. Cimarelli C, Mazzanti A, Palmieri G, Volpini E. Solvent-free asymmetric aminoalkylation of electron-rich aromatic compounds: stereoselective synthesis of aminoalkylnaphthols by crystallization-induced asymmetric transformation. J Org Chem 2001;66:4759-4765.
6. Liu DX, Zhang LC, Wang Q, Da CS, Zin ZQ, Wang R, Choi MKC, Chan ASC. The application of chiral aminonaphthols in the enantioselective addition of diethylzinc to aryl aldehydes. Org Lett 2001;3:2733-2735.
7. Cimarelli C, Palmieri G, Volpini E. A practical stereoselective synthesis of secondary and tertiary aminonaphthols: chiral ligands for enantioselective catalysts in the addition of diethylzinc to benzaldehyde. Tetrahedron: Asymmetry 2002;13:2417-2426.
8. Lu J, Xu X, Wang S, Wang C, Hu Y, Hu H. Novel preparation of non-racemic 1-[α-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their application as chiral ligands in the asymmetric addition of diethylzinc to aryl aldehydes. J Chem Soc Perkin Trans 1 2002;2900-2903.
9. Lu J, Xu X, Wang S, Wang C, He J, Hu Y, Hu H. Synthesis of chiral ligands derived from the Betti base and their use in the enantioselective addition of diethylzinc to aromatic aldehydes. Tetrahedron Lett 2002;43:8367-8369.
10. Ji JX, Qui LQ, Yip CW, Chan ASC. A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes. J Org Chem 2003;68:1589-1590.
11. Ji JX, Wu J, Au-Yeung TTL, Tip CW, Haynes RK, Chan ASC. Highly enantioselective phenyl transfer to aryl aldehydes catalyzed by easily accessible chiral tertiary aminonaphthol. J Org Chem 2005;70:1093-1095.
12. Dong Y, Li Rui, Lu J, Xu X, Wang X, Hu Y. An Efficient kinetic resolution of racemic betti base based on an enantioselective N, O-deketalization. J Org Chem 2005;70:8617-8620.
13. Wang X, Dong Y, Sun J, Xu X, Li R, Hu Y. Nonracemic betti base as a new chiral auxiliary: application to total syntheses of enantiopure (2S,6R)-dihydropinidine and (2S,6R)-isosolenopsins. J Org Chem 2005;70:1897-1900.
14. Szatmȧri I, Hetényi A, Lȧzár L, Fülöp F. Transformation reactions of the Betti base analog aminonaphthols. J Heterocyclic Chem 2004; 41:367-373.
15. Heydenreich M, Koch A, Klod S, Szatmári I, Fülöp F, Kleinpeter E. Synthesis and conformational analysis of naphth[1′,2′: 5,6][1,3] oxazino[3,2-c][1,3]benzoxazine and naphth[1′,2′:5, 6][1,3]oxazino[3,4-c] [1,3]benzoxazine derivatives. Tetrahedron 2006;62:11081-11089.
16. Desai NC, Shukla HK, Langalia NA, Thaker KA. Preparation and antibacterial activites of 2-aryl-3-[α-(2-hydroxy-1-naphthyl)benzyl]4- thiazolidinones. J Indian Chem Soc 1984;61:711-713.
17. Subramanian G. A practical approach to chiral separations by liquid chromatography. Weinheim: Wiley-VCH; 1994.
18. Jinno K. Chromatographic separations based on molecular recognition. New York: Wiley-VCH; 1997.
19. Beesley TE, Scott RPW. Chiral chromatography. New York: Wiley; 1998.
20. Oguni K, Oda H, Ichida A. Development of chiral stationary phases consisting of polysaccharide derivatives. J Chromatogr A 1995;694:91-100.
21. Yashima E. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation. J Chromatogr A 2001;906:105-125.
22. Franco P, Senso A, Oliveros L, Minguillón C. Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography. J Chromatogr A 2001;906:155-170.
23. Sztojkov-Ivanov A, Szatmári I, Péter A, Fülöp F. Structural and temperature effects in the high-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2-naphthol and 2-(α-aminobenzyl)-1-naphthol analogs. J Sep Sci 2005;28:2505-2510.
24. Berkecz R, Ilisz I, Sztojkov-Ivanov A, Szatmári I, Fülöp F, Armstrong DW, Péter A. High-performance liquid chromatographic enantioseparation of 1-(α-aminobenzyl)-2-naphthol and 2-(α- aminobenzyl)-1-naphthol analogs on a β-cyclodextrin-based chiral stationary phase. Chromatographia (in press).
25. Tóth D, Szatmári I, Fülöp F. Substituent effects in the ring-chain tautomerism of 1-alkyl-3-arylnaphth[1,2-e][1,3] oxazines. Eur J Org Chem 2006;20:4664-4669.
26. Gong Y, Kato K. Diastereoselective Friedel-Crafts reaction of α-trifluoromethyl imines derived from chiral amines. Tetrahedron: Asymmetry 2001;12:2121-2127.
27. Wang T, Wenslow RM Jr. Effect of alcohol mobile-phase modifiers on the structure and chiral selectivity of amylose tris(3,5-dimethylphenylcarbamate) chiral stationary phase. J Chromatogr A 2003;1015:99-110.
28. Meyer AZ. Molecular mechanics and molecular shape. IV. Shape and steric parameters. J Chem Soc Perkin Trans 2 1986;1567-1986.
29. Jabarpurwala K, Venkatachalam K, Kabadi M. Proton-ligand stability constants of some ortho-substituted phenols. J Inorg Nucl Chem 1964;26:1011-1026.
30. Sugimori T, Shibakawa K, Masuda H, Odani A, Yamauchi O. Ternary metal(II) complexes with tyrosine-containing dipeptides. Structures of copper(II) and palladium(II) complexes involving L-tyrosylglycine and stabilization of copper(II) complexes due to intramolecular aromatic ring stacking. Inorg Chem 1993;32:4951-4959.