NMR enantiodifferentiation of quaternary ammonium salts of Tröger base

Chirality

Volumn 21, Issue 9, 2009, Pages 809-817

  Michon, Christophe ^a   Gonçalves Farbos, Maria Héléna ^a   Lacour, Jérôme ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Asymmetric ion pairing; NMR chiral solvating agent; Pfeiffer effect; Quaternary ammonium ions; Solvent effect; Tr ger base

Indexed keywords

ACETONITRILE; ANION; BASE; BIS(TETRACHLOROBENZENEDIOLATO)MONO([1,1']BINAPHTHALENYL 2,2' DIOLATO)PHOSPHATE; QUATERNARY AMMONIUM DERIVATIVE; SODIUM CHLORIDE; UNCLASSIFIED DRUG;

CHEMICAL STRUCTURE; CHIRALITY; CONFERENCE PAPER; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SOLVATION;

EID: 70350552500     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20687     Document Type: Conference Paper

References (91)

1. Maruoka K, Ooi T. Enantioselective amino acid synthesis by chiral phase-transfer catalysis. Chem Rev 2003;103:3013-3028.
2. Lygo B, Andrews BI. Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: asymmetric alkylation of glycine imines. Acc Chem Res 2004;37:518-525.
3. O'Donnell MJ. The enantioselective synthesis of alpha-amino acids by phase-transfer catalysis with achiral schiff base esters. Acc Chem Res 2004;37:506-517.
4. Vachon J, Lacour J. Recent developments in enantioselective phase transfer catalysis using chiral ammonium salts. Chimia 2006;60:266-275. (Pubitemid 43874002)
5. Hashimoto T, Maruoka K. Recent development and application of chiral phase-transfer catalysts. Chem Rev 2007;107:5656-5682.
6. 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;21:2069-2081. (Pubitemid 30824078)
7. Uccello-Barretta G, Balzano F, Salvadori P. Enantiodiscrimination by NMR spectroscopy. Curr Pharm Des 2006;12:4023-4045.
8. Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117.
9. Duddeck H. 77Se NMR spectroscopy and its applications in chemistry. Annu Rep NMR Spectrosc 2004;52:105-166. (Pubitemid 39752336)
10. Wenzel TJ, Wilcox JD. Chiral reagents for the determination of enantiomeric excess and absolute configuration using NMR spectroscopy. Chirality 2003;15:256-270.
11. Rothchild R. NMR methods for determination of enantiomeric excess. Enantiomer 2000;5:457-471.
12. Parker D. NMR determination of enantiomeric purity. Chem Rev 1991;91:1441-1457.
13. Pirkle WH, Hoover DJ. NMR chiral solvating agents. Top Stereochem 1982;13:263-331.
14. Lacour J, Londez A, Goujon-Ginglinger C, Buß V, Bernardinelli G. Configurational ordering of cationic chiral dyes using a novel C2-symmetric hexacoordinated phosphate anion. Org Lett 2000;2:4185-4188.
15. Lacour J, Frantz R. New chiral anion mediated asymmetric chemistry. Org Biomol Chem 2005;3:15-19. (Pubitemid 40086155)
16. Lacour J, Linder D. Hexacoordinated phosphates: how to teach old chiral anions new asymmetric tricks. Chem Rec 2007;7:275-285.
17. 6+ (M = Rh, Ir, tpt = 2,4,6-tri(pyridin-4-yl)-1,3,5- triazine). Dalton Trans 2007;39:4457-4463.
18. Zalubovskis R, Bouet A, Fjellander E, Constant S, Linder D, Fischer A, Lacour J, Privalov T, Moberg C. Self-adaptable catalysts: substrate-dependent ligand configuration. J Am Chem Soc 2008;130:1845-1855. (Pubitemid 351238634)
19. Hebbe V, Londez A, Goujon-Ginglinger C, Meyer F, Uziel J, Juge S, Lacour J. NMR enantiodifferentiation of triphenylphosphonium salts by chiral hexacoordinated phosphate anions. Tetrahedron Lett 2003;44:2467-2471. (Pubitemid 36293586)
20. Herse C, Bas D, Krebs FC, Buergi T, Weber J, Wesolowski T, Laursen BW, Lacour J. A highly configurationally stable [4]heterohelicenium cation. Angew Chem Int Ed 2003;42:3162-3166.
21. Laleu B, Bernardinelli G, Chauvin R, Lacour J. Trimesitylmethyl- phosphonium cation. Supramolecular stereocontrol and simple enantiomerization mechanism determination. J Org Chem 2006;71:7412-7416. (Pubitemid 44452919)
22. Liu Y, Bonvallet PA, Vignon SA, Khan SI, Stoddart JF. Donor-acceptor pretzelanes and a cyclic bis[2]catenane homologue. Angew Chem Int Ed 2005;44:3050-3055.
23. 31P PGSE NMR diffusion studies on chiral organic salts: ion pairing and the dependence of a diffusion value on diastereomeric structure. Chem Eur J 2004;10:2912-2918.
24. Pasquato L, Herse C, Lacour J. NMR enantiodifferentiation of thiiranium cations by chiral hexacoordinated phosphate anions. Tetrahedron Lett 2002;43:5517-5520. (Pubitemid 34786501)
25. Pasquini C, Desvergnes-Breuil V, Jodry JJ, Dalla Cort A, Lacour J. Chiral anion-mediated asymmetric induction onto chiral diquats. Tetrahedron Lett 2002;43:423-426. (Pubitemid 34037916)
26. Vignon SA, Wong J, Tseng H-R, Stoddart JF. Helical chirality in donor-acceptor catenanes. Org Lett 2004;6:1095-1098.
27. Lacour J, Ginglinger C, Grivet C, Bernardinelli G. Synthesis and resolution of the configurationally stable tris(tetrachlorobenzenediolato) phosphate anion. Angew Chem Int Ed Engl 1997;36:608-609. (Pubitemid 27185246)
28. Heinrichs G, Kubik S, Lacour J, Vial L. Matched/mismatched interaction of a cyclic hexapeptide with ion pairs containing chiral cations and chiral anions. J Org Chem 2005;70:4498-4501. (Pubitemid 40734166)
29. Favarger F, Goujon-Ginglinger C, Monchaud D, Lacour J. Large scale synthesis and resolution of TRISPHAT [tris(tetrachlorobenzenediolato) phosphate(V)] Anion. J Org Chem 2004;69:8521-8524. (Pubitemid 39557227)
30. 31P NMR determination of the enantiomeric purity of quaternary phosphonium cations using TRISPHAT as chiral shift agent. Tetrahedron Lett 1998;39:7495-7498.
31. Lacour J, Vial L, Herse C. Efficient NMR enantiodifferentiation of chiral quats with BINPHAT anion. Org Lett 2002;4:1351-1354.
32. Gonçalves-Farbos M-H, Vial L, Lacour J. Enantioselective [1,2]-Stevens rearrangement of quaternary ammonium salts. A mechanistic evaluation. Chem Commun 2008;7:829-831.
33. Vial L, Gonçalves M-H, Morgantini P-Y, Weber J, Bernardinelli G, Lacour J. Unusual regio- and enantioselective [1,2]-Stevens rearrangement of a spirobi[dibenzazepinium] cation. Synlett 2004;9:1565-1568.
34. Vial L, Lacour J. Conformational preference and configurational control of highly symmetric spirobi[dibenzazepinium] cation. Org Lett 2002;4:3939-3942.
35. O'Farrell CM, Chudomel JM, Collins JM, Dignam CF, Wenzel TJ. Water-soluble calix[4]resorcinarenes with hydroxyproline groups as chiral NMR solvating agents. J Org Chem 2008;73:2843-2851.
36. Dignam CF, Zopf JJ, Richards CJ, Wenzel TJ. Water-soluble calix[4]resorcarenes as enantioselective NMR shift reagents for aromatic compounds. J Org Chem 2005;70:8071-8078.
37. Bergman SD, Frantz R, Gut D, Kol M, Lacour J. Effective chiral recognition among ions in polar medium. Chem Commun 2006:850-852. (Pubitemid 43255804)
38. Kostyanovsky RG, Kostyanovsky VR, Kadorkina GK, Lyssenko KA. Wedekind-fock-havinga salt Me(Et)N1(All)PhI-center dot CHCl3 as historically the first object for absolute asymmetric synthesis: spontaneous resolution, structure and absolute configuration. Mendeleev Commun 2001(1):1-5.
39. Tröger J. Ueber einige mittelst nascirenden formaldehydes entstehende Basen. J Prakt Chem 1887;36:225-245.
40. Prelog V, Wieland P. The resolution of Tröger's base into its optical antipodes, a note on the stereochemistry of trivalent nitrogen. Helv Chim Acta 1944;27:1127-1134.
41. Didier D, Sergeyev S. Analogues of Troger's base: recent developments and controversies. Targets Heterocycl Syst 2007;11:258-283.
42. Dolensky B, Elguero J, Kral V, Pardo C, Valik M. Current Troger's base chemistry. Adv Heterocycl Chem 2007;93:1-56.
43. Demeunynck M, Tatibouet A. Recent developments in Troger's base chemistry. Prog Heterocycl Chem 1999;11:1-20.
44. Pardo C, Alkorta I, Elguero J. A DFT study of the geometric, magnetic NMR chemical shifts and optical rotation properties of Troeger's bases. Tetrahedron: Asymmetry 2006;17:191-198. (Pubitemid 43226627)
45. Galasso V, Jones D, Modelli A. Molecular and electronic structure of Troger's bases. Chem Phys 2003;288:33-42.
46. Aamouche A, Devlin FJ, Stephens PJ. Structure, vibrational absorption and circular dichroism spectra, and absolute configuration of Troger's base. J Am Chem Soc 2000;122:2346-2354. (Pubitemid 30164647)
47. Wilen SH, Qi JZ, Williard PG. Resolution, asymmetric transformation, and configuration of Troeger's base. Application of Troeger's base as a chiral solvating agent. J Org Chem 1991;56:485-487.
48. Miller TR, Wagner EC. Some analogs of Troeger's base and related compounds. J Am Chem Soc 1941;63:832-836.
49. Spielman MA. The structure of Troeger's base. J Am Chem Soc 1935;57:583-585.
50. Faroughi M, Try AC, Klepetko J, Turner P. Changing the shape of Troger's base. Tetrahedron Lett 2007;48:6548-6551.
51. Didier D, Sergeyev S. Bromination and iodination of 6H,12H-5,11- methanodibenzo[b,f][1,5]diazocine: a convenient entry to unsymmetrical analogs of Troeger's base. Eur J Org Chem 2007;23:3905-3910.
52. Satishkumar S, Periasamy M. A convenient method for the synthesis and resolution of Troeger base. Tetrahedron: Asymmetry 2006;17:1116-1119.
53. Ishida Y, Ito H, Mori D, Saigo K. Regio/diastereo-controls of the Bingel-type biscyclopropanation of [60]fullerene by using bismalonates with a Troeger base analogue-derived tether. Tetrahedron Lett 2005;46:109-112.
54. Sergeyev S, Diederich F. Regio- and stereoselective tether-directed remote functionalization of C60 with derivatives of the Troger base. Angew Chem Int Ed 2004;43:1738-1740. (Pubitemid 39257879)
55. Jensen J, Strozyk M, Warnmark K. Influence of scale, stoichiometry and temperature on the synthesis of 2,8-dihalo analogs of Troger's base from the corresponding anilines and paraformaldehyde. J Heterocycl Chem 2003;40:373-375. (Pubitemid 36538885)
56. Harmata M, Kahraman M. Congeners of Troeger's base as chiral ligands. Tetrahedron: Asymmetry 2000;11:2875-2879. (Pubitemid 30645715)
57. Miyahara Y, Izumi K, Ibrahim AA, Inazu T. Novel C2 chiral diamine ligands derived from cyclic Troger bases. Tetrahedron Lett 1999;40:1705-1708. (Pubitemid 29087279)
58. Crossley MJ, Try AC, Walton R. Synthesis of accurate distance models of the primary donor - primary acceptor pair of bacterial photosynthetic reaction centers. Tetrahedron Lett 1996;37:6807-6810. (Pubitemid 26287987)
59. Valik M, Cejka J, Havlik M, Kral V, Dolensky B. Calix-Tris-Troger's bases - a new cavitand family. Chem Commun 2007;37:3835-3837. (Pubitemid 47429090)
60. Kim EI, Paliwal S, Wilcox CS. Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-pi interactions with implications for protein folding and molecular recognition. J Am Chem Soc 1998;120:11192-11193. (Pubitemid 28541204)
61. Crossley MJ, Mackay LG, Try AC. Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino-acid conformations in the bound-state. J Chem Soc Chem Commun 1995;18:1925-1927.
62. Tatibouët A, Demeunynck M, Andraud C, Collet A, Lhomme J. Synthesis and study of an acridine substituted Troger's base: preferential binding of the (-)-isomer to B-DNA. Chem Commun 1999;2:161-162. (Pubitemid 29054516)
63. Wilcox CS, Cowart MD. New approaches to synthetic receptors - synthesis and host properties of a water-soluble macrocyclic analog of Troger base. Tetrahedron Lett 1986;27:5563-5566.
64. Kiehne U, Bruhn T, Schnakenburg G, Frohlich R, Bringmann G, Lützen A. Synthesis, resolution, and absolute configuration of difunctionalized Troger's base derivatives. Chem Eur J 2008;14:4246-4255.
65. Khoshbin MS, Ovchinnikov MV, Mirkin CA, Golen JA, Rheingold AL. Metallomacrocycles incorporating a hemilabile Troeger's base derived ligand. Inorg Chem 2006;45:2603-2609.
66. Didier D, Tylleman B, Lambert N, Velde CMLV, Blockhuys F, Collas A, Sergeyev S. Functionalized analogues of Troger's base: scope and limitations of a general synthetic procedure and facile, predictable method for the separation of enantiomers. Tetrahedron 2008;64:6252-6262.
67. Zhong Q, He L, Beesley TE, Trahanovsky WS, Sun P, Wang C, Armstrong DW. Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography. J Chromatogr A 2006;1115:19-45.
68. Sajonz P, Gong X, Leonard WR Jr, Biba M, Welch CJ. Multiparallel chiral method development screening using an 8-channel microfluidic HPLC system. Chirality 2006;18:803-813. (Pubitemid 44619173)
69. Yamamoto C, Yashima E, Okamoto Y. Structural analysis of amylose Tris(3,5-dimethylphenylcarbamate) by NMR relevant to its chiral recognition mechanism in HPLC. J Am Chem Soc 2002;124:12583-12589.
70. Tobler E, Lammerhofer M, Wuggenig F, Hammerschmidt F, Lindner W. Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography. Electrophoresis 2002;23:462-476. (Pubitemid 34202093)
71. Trapp O, Schurig V. Stereointegrity of Troeger's base: gas-chromatographic determination of the enantiomerization barrier. J Am Chem Soc 2000;122:1424-1430. (Pubitemid 30120426)
72. Jung M, Boernsen KO, Francotte E. Dextrin sulfopropyl ether: a novel anionic chiral buffer additive for enantiomer separation by electrokinetic chromatography. Electrophoresis 1996;17:130-136. (Pubitemid 26060826)
73. Lenev DA, Lyssenko KA, Golovanov DG, Buss V, Kostyanovsky RG. Bis-ortho-substitution by methyl groups dramatically increases the racemization barrier of Troger bases. Chem Eur J 2006;12:6412-6418. (Pubitemid 44325293)
74. Trapp O, Trapp G, Kong JW, Hahn U, Vögtle F, Schurig V. Probing the stereointegrity of Troger's base - a dynamic electrokinetic chromatographic study. Chem Eur J 2002;8:3629-3634. (Pubitemid 34951450)
75. Lenev DA, Golovanov DG, Lyssenko KA, Kostyanovsky RG. Asymmetric nitrogen. Part 98. Configurationally stable methylates of methano- and ethano-Troger bases. Tetrahedron: Asymmetry 2006;17:2191-2194.
76. Häring M. Preparation of 5,11-endomethylenetetrahydrophenhomazines and 5-alkyltetrahydrophenhomazines. Helv Chim Acta 1963;46:2970-2982.
77. Monchaud D, Jodry JJ, Pomeranc D, Heitz V, Chambron J-C, Sauvage J-P, Lacour J. Ion-pair mediated asymmetric synthesis of a configurationally stable mononuclear tris(diimine) iron(II) complex. Angew Chem Int Ed 2002;41:2317-2319. (Pubitemid 34784596)
78. Monchaud D, Lacour J, Coudret C, Fraysse S. TRISPHAT salts. Efficient NMR chiral shift and resolving agents for substituted cyclometallated ruthenium bis(diimine) complexes. J Organomet Chem 2001;624:388-391. (Pubitemid 33667998)
79. Lacour J, Barchéchath S, Jodry JJ, Ginglinger C. Simple ion exchange procedure of common anions to TRISPHAT. Application to the purification of cationic species. Tetrahedron Lett 1998;39:567-570.
80. Weber E, Mueller U, Worsch D, Voegtle F, Will G, Kirfel A. Quaternary Troeger bases as new inclusion hosts: the first x-ray structures of a Troeger base and of a dioxane clathrate. J Chem Soc Chem Commun 1985;22:1578-1580.
81. Pfeiffer P, Quehl K. Uber einen neuen Effekt in Lösungen optischaktiver Substanzen. Chem Ber 1931;64:2667-2671.
82. Norden B, Tjerneld F. Binding of inert metal complexes to deoxyribonucleic acid detected by linear dichroism. FEBS Lett 1976;67:368-370.
83. Kirschner S, Ahmad N, Munir C, Pollock RJ. The Pfeiffer effect, outer-sphere complexation, and the absolute configuration of dissymmetric coordination compounds. Pure Appl Chem 1979;51:913-923.
84. Green MM, Khatri C, Peterson NC. A macromolecular conformational change driven by a minute chiral solvation energy. J Am Chem Soc 1993;115:4941-4942. (Pubitemid 23961159)
85. Yeh RM, Ziegler M, Johnson DW, Terpin AJ, Raymond KN. Imposition of chirality in a dinuclear triple-stranded helicate by ion pair formation. Inorg Chem 2001;40:2216-2217. (Pubitemid 32884438)
86. Lacour J, Jodry JJ, Monchaud D. Configurational ordering of a cationic dinuclear triple helicate by chiral TRISPHAT anions. Chem Commun 2001:2302-2303. (Pubitemid 33078289)
87. Bonnot C, Chambron J-C, Espinosa E. Simultaneous freezing of chirality and in-out conformation of a macropentacyclic cryptand by protonation. J Am Chem Soc 2004;126:11412-11413. (Pubitemid 39244937)
88. Yeh RM, Raymond KN. Supramolecular asymmetric induction in dinuclear triple-stranded helicates. Inorg Chem 2006;45:1130-1139.
89. Lacour J, Jodry JJ, Ginglinger C, Torche-Haldimann S. Diastereoselective Ion pairing of TRISPHAT anions and tris(4,4′-dimethylbipyridine) iron(II) Complex. Angew Chem Int Ed Engl 1998;37:2379-2380.
90. Pérollier C, Bernardinelli G, Lacour J. Sugar derived hexacoordinated phosphates: chiral anionic auxiliaries with general asymmetric efficiency. Chirality 2008;20:313-324. (Pubitemid 351303970)
91. Patonay T, Juhász-Tóth E, Bényei A. Base-induced coupling of alpha-azido ketones with aldehydes - an easy and efficient route to trifunctionalized synthons 2-azido-3-hydroxy ketones, 2-acylaziridines, and 2-acylspiroaziridines. Eur J Org Chem 2002;2:285-295.