Application of L-proline derivatives as chiral shift reagents for enantiomeric recognition of carboxylic acids

Chirality

Volumn 23, Issue 6, 2011, Pages 463-471

  Naziroglu, Hayriye Nevin ^a   Durmaz, Mustafa ^b   Bozkurt, Selahattin ^b   Sirit, Abdulkadir ^b  

^a KARAMANOGLU MEHMETBEY UNIVERSITY   (Turkey)

^b SELCUK UNIVERSITY   (Turkey)

Author keywords

carboxylic acid; chiral recognition; enantiomeric excess; L proline; NMR titration

Indexed keywords

1 METHYL 2 [(INDOLINYL)METHYL]PYRROLIDINE; 2 (N INDOLINYL)PYRROLIDINE 2 CARBOXAMIDE; 2 [(DIPHENYLMETHYL) 1 (1 METHYLPYRROLIDIN 2 YL)METHYL]PYRROLIDINE; 2 [(N DIPHENYLMETHYL)PYRROLIDINYL] 2 CARBOXAMIDE; CARBOXYLIC ACID; PROLINE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; ENANTIOMER; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; OSMOLARITY; PLOTS AND CURVES; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALANINE; AMINO ACIDS; CARBOXYLIC ACIDS; INDICATORS AND REAGENTS; LEAST-SQUARES ANALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NONLINEAR DYNAMICS; PROLINE; STEREOISOMERISM;

EID: 79958093120     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20948     Document Type: Article

References (60)

1. Jennings K, Diamond D,. Enantioselective molecular sensing of aromatic amines using tetra-(S)-di-2-naphthylprolinol calix[4]arene. Analyst 2001; 126: 1063-1067. (Pubitemid 32673288)
2. Dorsey JG, Cooper WT, Siles BA, Foley JP, Barth HG,. Liquid Chromatography: theory and methodology. Anal Chem 1996; 68: 515-568.
3. Schurig V, Nowotny HP,. Gas chromatographic separation of enantiomers on cyclodextrin derivatives. Angew Chem Int Ed 1990: 29; 939-957. (Pubitemid 20311867)
4. Grady T, Joyce T, Smyth MR, Haris SJ, Diamond D,. Chiral resolution of the enantiomers of phenylglycinol using (S)-di-naphthylprolinol calix[4]arene by capillary electrophoresis and fluorescence spectroscopy. Anal Commun 1998; 35: 123-125. (Pubitemid 128482572)
5. Fleischhauer J, Harmata M, Kahraman M, Koslowski A, Welch CJ,. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett 1997; 38: 8655-8658. (Pubitemid 27504415)
6. Kubo Y, Maeda S, Tokita S, Kubo M,. Colorimetric chiral recognition by a molecular sensor. Nature 1996; 382: 522-524. (Pubitemid 26260689)
7. Chappell JS,. Infrared discrimination of enantiomerically enriched and racemic samples of methamphetamine salts. Analyst 1997; 122: 755-760. (Pubitemid 27373063)
8. Grochowski J, Serda P,. Feasibility of chiral discrimination using X-ray anomalous scattering. Chirality 1993; 5: 277-281. (Pubitemid 23237744)
9. 1H-NMR spectroscopy. Forensic Sci Int 1992; 55: 131-137.
10. Seco JM, Quinoa E, Riguera R,. The assignment of absolute configuration by NMR. Chem Rev 2004; 104: 17-118.
11. Wenzel TJ, Wilcox JD,. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 2003; 15: 256-270. (Pubitemid 36268461)
12. Parker D,. NMR determination of enantiomeric purity. Chem Rev 1991; 91: 1441-1457.
13. Machida Y, Nishi H, Nakamura K,. Nuclear magnetic resonance studies for the chiral recognition of the novel chiral stationary phase derived from 18-crown-6 tetracarboxylic acid. J Chromatogr A 1998; 810: 33-41. (Pubitemid 28288225)
14. Schneider H-J, Hacket F, Rudiger V, Ikeda H,. NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 1998; 98: 1755-1785. (Pubitemid 128633436)
15. Chankvetadze B, Blaschke G,. Enantioseparations in capillary electromigration techniques: recent developments and future trends. J Chromatogr A 2001; 906: 309-363.
16. Lee W, Bang E, Baek C-S, Lee W,. Chiral discrimination studies of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid by high-performance liquid chromatography and NMR spectroscopy. Magn Reson Chem 2004; 42: 389-395. (Pubitemid 40012524)
17. Dodziuk H, Kozminski W, Ejchart A,. NMR studies of chiral recognition by cyclodextrins. Chirality 2004; 16: 90-105. (Pubitemid 38134072)
18. Bruylants G, Bresson C, Boisdenghien A, Pierard F, Mesmaeker AKD, Lacour J, Bartik K,. Comparison of the NMR enantiodifferentiation of a chiral ruthenium(II) complex of C2 symmetry using the TRISPHAT anion and a lanthanide shift reagent. New J Chem 2003; 27: 748-751. (Pubitemid 36469892)
19. Wang W, Ma F, Shen X, Zhang C,. New chiral auxiliaries derived from (S)-a-phenylethylamine as chiral solvating agents for carboxylic acids. Tetrahedron: Asymmetry 2007; 18: 832-837. (Pubitemid 46669983)
20. Yang X, Wang G, Zhong C, Wua X, Fu E,. Novel NMR chiral solvating agents derived from (1R,2R)-diaminocyclohexane: synthesis and enantiodiscrimination for chiral carboxylic acids. Tetrahedron: Asymmetry 2006; 17: 916-921.
21. Port A, Virgili A, Alvarez-Larena A, Piniella JF,. Preparation of enantiomers of 1-(1-naphthyl)-2,2-dimethylpropylamine and their behaviour as chiral solvating agents: study of diastereochemic association by Job's plots and intermolecular NOE measurements. Tetrahedron: Asymmetry 2000; 11: 3747-3757.
22. Enders D, Thomas CR, Runsink J,. 5-Amino-4-aryl-2,2-dimethyl-1,3-dioxans: application as chiral NMR shift reagents and derivatizing agents for acidic compounds. Tetrahedron: Asymmetry 1999; 10: 323-326. (Pubitemid 29119497)
23. Peña C, González-Sabín J, Alfonso I, Rebolledo F, Gotor V,. Cycloalkane-1,2-diamine derivatives as chiral solvating agents. Study of the structural variables controlling the NMR enantiodiscrimination of chiral carboxylic acids. Tetrahedron 2008; 64: 7709-7719.
24. Peña C, González-Sabín J, Alfonso I, Rebolledo F, Gotor V,. New pincer-like receptor derived from trans-cyclopentane-1,2-diamine as a chiral shift reagent for carboxylic acids. Tetrahedron: Asymmetry 2007; 18: 1981-1985. (Pubitemid 47393620)
25. Cuevas F, Ballester P, Pericas MA,. Structurally simple, modular amino alcohols for the recognition of carboxylic acids. Application to the development of a new chiral solvating agent. Org Lett 2005; 7: 5485-5487. (Pubitemid 41775162)
26. Satishkumar S, Periasamy M,. Chiral recognition of carboxylic acids by Tröger's base derivatives. Tetrahedron: Asymmetry 2009; 20: 2257-2262.
27. Busto E, González-Úlvarez A, Gotor-Fernández V, Alfonso I, Gotor V,. Optically active macrocyclic hexaazapyridinophanes decorated at the periphery: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids. Tetrahedron 2010; 66: 6070-6077.
28. Ma F, Ai L, Shen X, Zhang C,. New macrocyclic compound as chiral shift reagent for carboxylic acids. Org Lett 2007; 9: 125-127.
29. Ma F, Shen X, Ming X, Wang J, Ou-Yang J, Zhang C,. The novel macrocyclic compounds as chiral solvating agents for determination of enantiomeric excess of carboxylic acids. Tetrahedron: Asymmetry 2008; 19: 1576-1586.
30. Tanaka K, Fukuda N,. 'Calixarene-like' chiral amine macrocycles as novel chiral shift reagents for carboxylic acids. Tetrahedron: Asymmetry 2009; 20: 111-114.
31. Li B, Yang X, Wu X, Luo Z, Zhong C, Fu E,. Enantioselective recognition for carboxylic acids by novel chiral macrocyclic polyamides derived from L-/D-tartaric Acid. Supramol Chem 2006; 18: 507-513. (Pubitemid 44352829)
32. Altava B, Isabel Burguete M, Carbõ N, Escorihuela J, Luis SV,. Chiral bis(amino amides) as chiral solvating agents for enantiomeric excess determination of α-hydroxy and arylpropionic acids. Tetrahedron: Asymmetry 2010; 21: 982-989.
33. Yuan Q, Fu E, Wu X, Fang M, Xue P, Wua C, Chen J,. A convenient synthesis of chiral dioxocyclens and application as chiral solvating agents. Tetrahedron Lett 2002; 43: 3935-3937. (Pubitemid 34463067)
34. Ema T, Tanida D, Sakai T,. Versatile and practical macrocyclic reagent with multiple hydrogen-bonding sites for chiral discrimination in NMR. J Am Chem Soc 2007; 129: 10591-10596. (Pubitemid 47330279)
35. Voyer N, Cote S, Biron E, Beaumont M, Chaput M, Levac S,. Chiral recognition of carboxylic acids by bis-crown ether peptides. J Supramol Chem 2001; 1: 1-5. (Pubitemid 33619757)
36. Voyer N, Guerin B,. Chiral recognition ability of peptide-based molecular receptors. Chem Commun 1997: 2329-2330. (Pubitemid 127696275)
37. 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: 1242-1248.
38. Shirakawa S, Moriyama A, Shimizu S,. Synthesis, optical resolution and enantiomeric recognition ability of novel, inherently chiral calix[4]arenes: trial application to asymmetric reactions as organocatalysts. Eur J Org Chem 2008: 5957-5964.
39. Zheng YS, Zhang C,. Exceptional chiral recognition of racemic carboxylic acids by calix[4]arenes bearing optically pure α,β-amino alcohol groups. Org Lett 2004; 6: 1189-1192. (Pubitemid 38692020)
40. Liu XX, Zheng YS,. Chiral nitrogen-containing calix[4]crown-an excellent receptor for chiral recognition of mandelic acid. Tetrahedron Lett 2006; 47: 6357-6360.
41. Demirtas HN, Bozkurt S, Durmaz M, Yilmaz M, Sirit A,. Synthesis of new chiral calix[4]azacrowns for enantiomeric recognition of carboxylic acids. Tetrahedron: Asymmetry 2008; 19: 2020-2025.
42. Durmaz M, Yilmaz M, Sirit A,. Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids. Org Biomol Chem 2011; 9: 571-580.
43. Shirakawa S, Moriyama A, Shimizu S,. Design of a novel inherently chiral calix[4]arene for chiral molecular recognition. Org Lett 2007; 9: 3117-3119.
44. Yang X, Wu X, Fang M, Yuan Q, Fu E,. Novel rigid chiral macrocyclic dioxopolyamines derived from L-proline as chiral solvating agents for carboxylic acids. Tetrahedron: Asymmetry 2004; 15: 2491-2497. (Pubitemid 39164144)
45. Baily DJ, O'Hagan D, Tavasli M,. A short synthesis of (S)-2-(diphenylmethyl)pyrrolidine, a chiral solvating agent for NMR analysis. Tetrahedron: Asymmetry 1997; 8: 149-153. (Pubitemid 27039335)
46. Karakucuk A, Durmaz M, Sirit A, Yilmaz M, Demir AS,. Synthesis and chiral recognition properties of two novel chiral calix[4]arene tartaric ester derivatives. Tetrahedron: Asymmetry 2006; 17: 1963-1968. (Pubitemid 44205458)
47. Demirtas HN, Bozkurt S, Durmaz M, Yilmaz M, Sirit A,. Chiral calix[4]azacrowns for enantiomeric recognition of amino acid derivatives. Tetrahedron 2009; 65: 3014-3018.
48. Kocabas E, Durmaz M, Alpaydin S, Sirit A, Yilmaz M,. Chiral mono and diamide derivatives of calix[4]arene for enantiomeric recognition of chiral amines. Chirality 2008; 20: 26-34. (Pubitemid 350308708)
49. Durmaz M, Alpaydin S, Sirit A, Yilmaz M,. Chiral Schiff base derivatives of calix[4]arene: synthesis and complexation studies with chiral and achiral amines. Tetrahedron: Asymmetry 2006; 17: 2322-2327. (Pubitemid 44485498)
50. Durmaz M, Alpaydin S, Sirit A, Yilmaz M,. Enantiomeric recognition of amino acid derivatives by chiral Schiff bases of calix[4]arene. Tetrahedron: Asymmetry 2007; 18: 900-905. (Pubitemid 46669984)
51. Bozkurt S, Durmaz M, Yilmaz M, Sirit A,. Calixarene-based chiral phase-transfer catalysts derived from cinchona alkaloids for enantioselective synthesis of α-amino acids. Tetrahedron: Asymmetry 2008; 19: 618-623.
52. Job P,. Formation and stabitity of inorganic complexes in solution. Ann Chim (Paris) 1928; 9: 113-203.
53. Kobayashi S, Horibe M,. Chiral lewis acid controlled synthesis (CLAC Synthesis): chiral lewis acids influence the reaction course in asymmetric aldol reactions for the synthesis of enantiomeric dihydroxythioester derivatives in the presence of chiral diamines derived from L-proline. Chem Eur J 1997; 3: 1472-1481. (Pubitemid 27383712)
54. Huang J, Corey EJ,. A mechanistically guided design leads to the synthesis of an efficient and practical new reagent for the highly enantioselective, catalytic dihydroxylation of olefins. Org Lett 2003; 5: 3455-3458. (Pubitemid 37487436)
55. Terakado D, Oriyama T,. Catalytic asymmetric acylation of alcohols using a chiral 1,2-diamine derived from (S)-proline: (1S,2S)-trans-1-benzoyloxy-2- bromocyclohexane. Org Synth 2006; 83: 70-79.
56. Alcon MJ, Iglesias M, Sanchez F, Viani I,. Synthesis of Rh(I) and Ir(I) complexes with chiral C2-multitopic ligands. J Organomet Chem 2001; 634: 25-33.
57. List B,. Proline-catalyzed asymmetric reactions. Tetrahedron 2002; 58: 5573-5590. (Pubitemid 34722894)
58. Zhang D, Yuan C,. An enantioselective nucleophilic addition of α,β-unsaturated trifluoromethylketones catalyzed by L-proline derivatives. Tetrahedron 2008; 64: 2480-2488.
59. Macomber RS,. An introduction to NMR titration for studying rapid reversible complexation. J Chem Ed 1992; 69: 375-378.
60. Fielding L,. Determination of association constants (Ka) from solution NMR data. Tetrahedron 2000; 56: 6151-6170. (Pubitemid 30646746)