Determination of absolute configurations by X-ray crystallography and 1H NMR anisotropy

Chirality

Volumn 20, Issue 5, 2008, Pages 691-723

  Harada, Nobuyuki ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

1H NMR anisotropy; Absolute configuration; Camphorsultam dichlorophthalic acid (CSDP acid); Chiral 1H NMR anisotropy reagents (CAR); Chiral X ray reference reagents (CXR); Internal reference; X ray crystallography

Indexed keywords

2 METHOXY 2 (1 NAPHTHYL)PROPIONIC ACID; 4 METHYLDIPHENHYDRAMINE; ALCOHOL DERIVATIVE; AMINE; ANTIHISTAMINIC AGENT; BENZATROPINE; CAMPHORSULTAM DICHLOROPHTHALIC ACID; CHLORBENZOXAMINE; CHLOROBENZTROPINE; CLEMASTINE; KAT 2003; MENTHOL; PHTHALIC ACID DERIVATIVE; PROPIONIC ACID DERIVATIVE; THYROID HORMONE DERIVATIVE; TOFENACIN;

ANISOTROPY; CHIRALITY; CIRCULAR DICHROISM; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REVIEW; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALCOHOLS; ANISOTROPY; CARBOXYLIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CIRCULAR DICHROISM; CRYSTALLOGRAPHY, X-RAY; FULLERENES; HYDROGEN; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 43249096726     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20478     Document Type: Review

References (98)

1. Bijvoet JM, Peerdeman AF, van Bommel AJ. Determination of the absolute configuration of optically active compounds by means of X-rays. Nature 1951;168:271-272.
2. Flack HD. On enantiomorph-polarity estimation. Acta Crystallogr A 1983;39:876-881.
3. Mason SF. The absolute configuration of calycanthine. Proc Chem Soc 1962;362-363.
4. Harada N, Nakanishi K. A method for determining the chiralities of optically active glycols. J Am Chem Soc 1969;91:3989-3991.
5. Harada N, Nakanishi K. Circular dichroic spectroscopy - exciton coupling in organic stereochemistry. Mill Valley, CA: University Science Books; 1983.
6. Berova N, Nakanishi K. Exciton chirality method: principles and applications. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism, principles and applications. New York: Wiley-VCH; 2000. Chapter 12.
7. Kemp C, Mason SF. The absorption and circular dichroism spectra and the absolute configuration of (+)-1-fluoro-12-methylbenzo[c]phenanthrene. Tetrahedron 1966;22:629-635.
8. Harada N. Circular dichroism spectroscopy and absolute stereochemistry of biologically active compounds. In: Cooper R, Snyder JK, editors. The biology-chemistry interface. New York: Marcel Dekker; 1999. Chapter 6, p 139-190.
9. Harada N. Circular dichroism of twisted π-electron systems: theoretical determination of the absolute stereochemistry of natural products and chiral synthetic organic compounds. In: Berova N, Nakanishi K, Woody RW, editors. Circular dichroism, principles and applications. New York: Wiley-VCH; 2000. Chapter 15.
10. Cheeseman JR, Frisch MJ, Devlin FJ, Stephens PJ. Ab initio calculation of atomic axial tensors and vibrational rotational strengths using density functional theory. Chem Phys Lett 1996;252:211-220.
11. Polavarapu PL. Vibrational spectra: Principles and applications with emphasis on optical activity. Amsterdam: Elsevier; 1998.
12. Freedman TB, Cao X, Dukor RK, Nafie LA. Absolute configuration determination of chiral molecules in the solution state using vibrational circular dichroism. Chirality 2003;15:743-758.
13. Barron LD. Molecular light scattering and optical activity, 2nd ed. Cambridge: Cambridge University Press; 2004.
14. Harada N, Soutome T, Murai S, Uda H. A chiral probe useful for optical resolution and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. Tetrahedron: Asymmetry 1993;4:1755-1758.
15. Harada N, Soutome T, Nehira T, Uda H, Oi S, Okamura A, Miyano S. Revision of the absolute configurations of [8]paracyclophane-10-carboxylic and 15-methyl[10]paracyclo-phane-12-carboxylic acids. J Am Chem Soc 1993;115:7547-7548.
16. Harada N, Hattori T, Suzuki T, Okamura A, Ono H, Miyano S, Uda H. Absolute stereochemistry of 1-(9-phenanthryl)-2-naphthoic acid as determined by CD and X-ray methods. Tetrahedron: Asymmetry 1993;4:1789-1792.
17. Hattori T, Harada N, Oi S, Abe H, Miyano S. 1,12-Dioxa[12] (1,4)naphthalenophane-14-carboxylic acid: practical synthesis, resolution and absolute configuration of the enantiomers. Tetrahedron: Asymmetry 1995;6:1043-1046.
18. Harada N. Chiral auxiliaries powerful for both enantiomer resolution and determination of absolute configuration by X-ray crystallography. In: Denmark SE, Siegel JS, editors. Topics in stereochemistry, Vol .25. New Jersey: John Wiley; 2000. Chapter 6, p 177-203.
19. 1H NMR anisotropy methods. In: Francotte E, Lindner W, editors. Chirality in drug research. Weinheim, Germany: Wiley-VCH; 2006. Chapter 9, p 283-321.
20. 1H NMR anisotropy methods. In: Busch KW, Busch MA, editors. Chiral analysis. Amsterdam: Elsevier; 2006. Chapter 18.
21. Fujita T, Kuwahara S, Watanabe M, Harada N. Crystalline state conformation of 2-methoxy-2-(1-naphthyl)propionic acid ester. Enantiomer 2002;7:219-224.
22. 1H NMR anisotropy tools. Eur J Org Chem 2007;1827-1840.
23. Toda F. Isolation and optical resolution of materials utilizing inclusion crystallization. Top Curr Chem 1987;140:43-69.
24. Toda F, Tanaka K, Miyahara I, Akutsu S, Hirotsu K. Role of methanol in chiral combinations of host-guest molecules in the inclusion crystal: structure determination by X-ray crystallography. J Chem Soc Chem Commun 1994;1795-1796.
25. Toda F, Tanaka K, Watanabe M, Abe T, Harada N. Enantiomer resolution by crystallization with chiral hosts: application to monoterpenes, verbenone and apoverbenone. Tetrahedron: Asymmetry 1995;6:1495-1498.
26. 60 fullerene cis-3 bisadducts by X-ray crystallography and circular dichroism. Angew Chem Int Ed 2005;44:2262-2265.
27. Harada N, Koumura N, Feringa BL. Chemistry of unique chiral olefins. 3. Synthesis and absolute stereochemistry of trans- and cis-1, 1′,2,2′,3,3′,4,4′-octahydro-3,3′-dimethyl-4, 4′-biphenanthrylidenes. J Am Chem Soc 1997;119:7256-7264.
28. Fujita T, Kuwahara S, Harada N. A new model of light powered chiral molecular motor with higher speed of rotation. 1. Synthesis and absolute stereostructure. Eur J Org Chem 2005;4533-4543.
29. Harada N, Fujita K, Watanabe M. Molecular chirality by isotopic substitution. Synthesis, absolute configuration, and CD spectra of chiral diphenylmethanols. Enantiomer 1998;3:64-70.
30. Nakamura E, Isobe H, Tokuyama H, Sawamura M. Regio- and diastereo-controlled double cycloaddition to [60]fullerene: one-step synthesis of Cs and C2 chiral organofullerenes with new tris-annulating reagent. Chem Commun 1996;1747-1748.
31. Taki M, Sugita S, Nakamura Y, Kawashima E, Yashima E, Okamoto Y, Nishimura J. Selective functionalization on [60]fullerene governed by tether length. J Am Chem Soc 1997;119:926-932.
32. Nierengarten JF, Habicher T, Kessinger R, Cardullo F, Diederich F, Gramlich V, Gisselbrecht JP, Boudon C, Gross M. Macrocyclization on the fullerene core: direct regio- and diastereoselective multi-functionalization of [60]fullerene, and synthesis of fullerene-dendrimer derivatives. Helv Chim Acta 1997;80:2238-2276.
33. 1)-bisadducts: CD spectra of enantiomers and diastereospecific synthesis. Enantiomer 1998;3:231-239.
34. Ishi-i T, Nakashima K, Shinkai S, Ikeda A. Saccharide libraries as potential templates for regio- and chiroselective introduction of two functional groups into [60]fullerene. J Org Chem 1999;64:984-990.
35. Nakamura Y, O-kawa K, Nishimura J. Biscycloaddition to [60]fullerene: regioselectivity and its control with templates. Bull Chem Soc Jpn 2003;76:865-882.
36. Goto H, Harada N, Crassous J, Diederich F. Absolute configuration of chiral fullerenes and covalent derivatives from their calculated circular dichroism. J Chem Soc Perkin Trans 2 1998:1719-1723.
37. 60: regio- and stereoselective synthesis, exciton chirality coupling, and determination of the absolute configuration, and first observation of exciton coupling between fullerene chromophores in a chiral environment. Helv Chim Acta 2000;83:3069-3096.
38. 60 fullerene bis-adducts. Enantiomer 2002;7:23-32.
39. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α- trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973;95:512-519.
40. Trost BM, Belletire JL, Godleski S, McDougal PG, Balkovec JM, Baldwin JJ, Christy ME, Ponticello GS, Varga SL, Springer JP. On the use of the O-methylmandelate ester for establishment of absolute configuration of secondary alcohols. J Org Chem 1986;51:2370-2374.
41. Ohtani I, Kusumi T, Kashman Y, Kakisawa H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J Am Chem Soc 1991;113:4092-4096.
42. Kusumi T, Takahashi H, Hashimoto T, Kan Y, Asakawa Y. Determination of the absolute configuration of ginnol, a long-chain aliphatic alcohol, by use of a new chiral anisotropic reagent Chem Lett 1994;1093-1094.
43. Yamase H, Ooi T, Kusumi T. Determination of the absolute configuration of linear secondary alcohols adopting one enantiomer of the chiral anisotropic reagents, methoxy(1- and 2-naphthyl)acetic acids. Tetrahedron Lett 1998;39:8113-8116.
44. Seco JM, Latypov Sh, Quinoa E, Riguera R. New chirality recognizing reagents for the determination of absolute stereochemistry and enantiomeric purity by NMR. Tetrahedron Lett 1994;35:2921-2924.
45. Seco JM, Latypov Sh, Quinoa E, Riguera R. Determining factors in the assignment of the absolute configuration of alcohols by NMR. The use of anisotropic effects on remote positions. Tetrahedron 1997;53:8541-8564.
46. Seco JM, Tseng LH, Godejohann M, Quinoa E, Riguera R. Simultaneous enantioresolution and assignment of absolute configuration of secondary alcohols by directly coupled HPLC-NMR of 9-AMA esters. Tetrahedron: Asymmetry 2002;13:2149-2153.
47. Seco JM, Quinoa E, Riguera R. The assignment of absolute configuration by NMR. Chem Rev 2004;104:17-117.
48. Seco JM, Quinoa E, Riguera R. The assignment of absolute configurations by NMR of arylmethoxyacetate derivatives: is this methodology being correctly used? Tetrahedron: Asymmetry 2000;11:2781-2791.
49. Takahashi T, Fukuishima A, Tanaka Y, Takeuchi Y, Kabuto K, Kabuto C. CFTA, a new efficient agent for determination of absolute configurations of chiral secondary alcohols. Chem Commun 2000;787-788.
50. Fujiwara T, Sasaki M, Omata K, Kabuto C, Kabuto K, Takeuchi Y. An efficient procedure for the resolution of α-cyano-α-fluoro-p- tolylacetic acid (CFTA) via the diastereomeric N-carbobenzyloxy- cis-1-amino-2-indanol esters. Tetrahedron: Asymmetry 2004;15:555-563.
51. Kuwahara S, Fujita K, Watanabe M, Harada N, Ishida T. Enantioresolution and absolute stereochemistry of 2-(1-naphthyl)propane-1,2-diol and related compounds. Enantiomer 1999;4:141-145.
52. 1H NMR anisotropy method. Tetrahedron: Asymmetry 2000;11:1249-1253.
53. 1H NMR anisotropy method. Chirality 2002;14:81-84.
54. 1H NMR shift reagent, MαNP acid. Use of HPLC-CD detector. Chirality 2003;15:295-299.
55. 1H NMR anisotropy method with a novel chiral auxiliary, MαNP acid. Chirality 2004;16:13-21.
56. 1H NMR anisotropy method. Chirality 2004;16:569-585.
57. Kasai Y, Shimanuki K, Kuwahara S, Watanabe M, Harada N. Preparation of enantiopure Wieland-Miescher ketone and derivatives by the MαNP acid method. Substituent effect on the HPLC separation. Chirality 2006;18:177-187.
58. 1H NMR anisotropy tools. Aromatic geometry and solvent effects on Δδ values. Eur J Org Chem 2006;1811-1826.
59. 1H NMR anisotropy method. J Synth Org Chem 2004;62:1114-1127.
60. 1H NMR and/or MS spectrometry with complete removal of the kinetic resolution effect. Org Lett 2002; 4:2699-2702.
61. Ichikawa A, Ono H, Harada N. Synthesis and analytical properties of (S)-(+)-2-methoxy-2-(9-phenanthryl)propionic acid. Tetrahedron: Asymmetry 2003;14:1593-1597.
62. Ichikawa A, Ono H, Harada N. Stereochemical studies of chiral resolving agents, M9PP and H9PP acids. Chirality 2004;16:559-567.
63. Wenzel TJ. Discrimination of chiral compounds using NMR spectroscopy. USA: John Wiley; 2007.
64. Harada N, Koumura N, Robillard M. Chiral dichlorophthalic acid amide: an improved chiral auxiliary useful for enantioresolution and X-ray crystallographic determination of absolute stereochemistry. Enantiomer 1997;2:303-309.
65. Harada N, Nehira T, Soutome T, Hiyoshi N, Kido F. Chiral phthalic acid amide, a chiral auxiliary useful for enantiomer resolution and X-ray crystallographic determination of the absolute stereochemistry of alcohols. Enantiomer 1996;1:35-39.
66. Kosaka M, Kuwahara S, Watanabe M, Harada N, Job GE, Pirkle WH. Comparison of CD spectra of (2-methylphenyl)- and (2,6-dimethylphenyl)-phenylmethanols leads to erroneous absolute configurations. Enantiomer 2002;7:213-218.
67. Harada N, Fujita K, Watanabe M. Enantioresolution and absolute stereochemistry of diarylmethanols. Enantiomer 1997;2:359-366.
68. 13C substituted chiral diphenylmethanol. J Phys Org Chem 2000;13:422-425.
69. Kuwahara S, Watanabe M, Harada N, Koizumi M, Ohkuma T. Enantioresolution and absolute stereochemistry of o-substituted diphenylmethanols. Enantiomer 2000;5:109-114.
70. Watanabe M, Kuwahara S, Harada N, Koizumi M, Ohkuma T. Enantioresolution by the chiral phthalic acid method: absolute configurations of (2-methylphenyl)phenylmethanol and related compounds. Tetrahedron: Asymmetry 1999;10:2075-2078.
71. Kosaka M, Watanabe M, Harada N. Enantioresolution by the chiral phthalic acid method: Absolute configurations of substituted benzylic alcohols. Chirality 2000;12:362-365.
72. Harada N, Hiyoshi N, Vassilev VP, Hayashi T. Synthesis, circular dichroism, and absolute stereochemistry of 1,1′:4′,1″- ternaphthalene compounds. Chirality 1997;9:623-625.
73. Harada N, Vassilev VP, Hiyoshi N. Absolute configuration and conformation of 1,1′:4′,1″-ternaphthalene compounds as determined by X-ray crystallography. Enantiomer 1997;2:123-126.
74. 1H NMR anisotropy methods. Chirality 2004;16:22-35.
75. 1H NMR anisotropy methods. Chirality 2003;15:324-328.
76. ter Wiel MKJ, van Delden RA, Meetsma A, Feringa BL. Increased speed of rotation for the smallest light-driven molecular motor. J Am Chem Soc 2003;125:15076-15086.
77. Goto J, Hasegawa M, Nakamura S, Shimada K, Nambara T. New derivatization for liquid chromatographic resolution of amino acid enantiomers. Chem Pharm Bull 1977;25:847-849.
78. Goto J, Hasegawa M, Nakamura S, Shimada K, Nambara T. New derivatization reagents for the resolution of amino acid enantiomers by high-performance liquid chromatography. J Chromatogr 1978;152: 413-419.
79. Ichikawa A. Application of αMNPA to stereochemical studies of monoterpene alcohol. Chirality 1999;11:70-74.
80. Akasaka K, Gyimesi-Forras K, Lammerhofer M, Fujita T, Watanabe M, Harada N, Lindner W. Investigations of molecular recognition aspects related to the enantiomer separation of 2-methoxy-2-(1-naphthyl)propionic acid using quinine carbamate as chiral selector: an NMR and FT-IR spectroscopic as well as X-ray crystallographic study. Chirality 2005;17:544-555.
81. 1H NMR anisotropy reagent. Chirality 2007; 19: 335-343.
82. 1H NMR anisotropy method. Tetrahedron: Asymmetry 1999;10:4075-4078.
83. 1H NMR anisotropy method. Tetrahedron: Asymmetry 2000;11:2669-2675.
84. Ichikawa A, Ono H, Hiradate S, Watanabe M, Harada N. Absolute configuration of 2-methoxy-2-(1-naphthyl)propionic and 2-methoxy-2-(2-naphthyl) propionic acids as determined by the phenylglycine methyl ester (PGME) method. Tetrahedron: Asymmetry 2002;13:1167-1172.
85. Gyimesi-Forras K, Akasaka K, Lammerhofer M, Fujita T, Taji H, Watanabe M, Harada N, Lindner W. Enantiomer separation of a powerful chiral auxiliary, 2-methoxy-2-(1-naphthyl)propionic acid by liquid chromatography using chiral anion exchanger type stationary phases in polar-organic mode; Investigation of molecular recognition aspects. Chirality 2005;17:S134-S142.
86. Naito J, Yamamoto Y, Akagi M, Sekiguchi S, Watanabe M, Harada N. Unambiguous determination of the absolute configurations of acetylene alcohols by combination of the Sonogashira reaction and the CD exciton chirality method - Exciton coupling between phenylacetylene and benzoate chromophores. Monatsh Chem 2005;136:411-445.
87. Kosaka M, Sekiguchi S, Naito J, Kuwahara S, Watanabe M, Harada N, Hiroi K. Synthesis of enantiopure phthalides including 3-butylphthalide, a fragrance component of celery oil, and determination of their absolute configurations. Chirality 2005;17:218-232.
88. Fujita T, Obata K, Kuwahara S, Miura M, Nakahashi A, Monde K, Decatur J, Harada N. (R)-(+)-[VCD(+)945]-4-Ethyl-4-methyloctane, the simplest chiral saturated hydrocarbon with a quaternary stereogenic center. Tetrahedron Lett 2007;48:4219-4222.
89. Okumura Y, Ando A, William Stevens R, Shimizu M. Efficient and practical synthesis of both enantiomers of 3-phenylcyclopentanol derivatives. Tetrahedron 2002;58:8729-8736.
90. Imamura Y, Takikawa H, Sasaki M, Mori K. Triterpenoid total synthesis. Synthesis and absolute configuration of mispyric acid. Org Biomol Chem 2004;2:2236-2244.
91. Ichikawa A, Ono H. Preparation of single-enantiomer semiochemicals using 2-methoxy-2-(1-naphthyl)propionic acid and 2-methoxy-2-(9-phenanthryl)propionic acid. Tetrahedron: Asymmetry 2005; 16:2559-2568.
92. Ichikawa A, Ono H. Preparation of single-enantiomer 2-methyl-4-heptanol, a pheromone of Metamasius hemipterus, using (S)-2-methoxy-2-(1- naphthyl)propionic acid. J Chromatog A 2006;1117:38-46.
93. Ochi T, Sakamoto M, Minamida A, Suzuki K, Ueda T, Une T, Toda H, Matsumoto K, Terauchi Y. Syntheses and properties of the major hydroxy metabolites in humans of blonanserin AD-5423, a novel antipsychotic agent. Bioorg Med Chem Lett 2005; 15:1055-1059.
94. Narumi F, Hattori T, Yamabuki W, Kabuto C, Kameyama H. Resolution of inherently chiral anti-O,O′-dialkylated calix[4]arenes and determination of their absolute stereochemistries by CD and X-ray methods. Tetrahedron: Asymmetry 2005;16:793-800.
95. Fujita Y, Oguri H, Oikawa H. The relative and absolute configuration of PF1140. J Antibiot 2005;58:425-427.
96. Helmchen G, Nill G, Flockerzi D, Schule W, Youssef MSK. Extreme liquid chromatographic separation effects in the case of diastereomeric amides containing polar substituents. Angew Chem Int Ed Engl 1979;18:62-63.
97. Helmchen G, Nill G, Flockerzi D, Youssef MSK. Preparative scale directed resolution of enantiomeric carboxylic acids and lactones via liquid chromatography and neighboring-group assisted hydrolysis of diastereomeric amides. Angew Chem Int Ed Engl 1979;18:63-65.
98. Arita S, Yabuuchi T, Kusumi T. Resolution of 1- and 2- naphthylmethoxyacetic acids, NMR reagents for absolute configuration determination, by use of L-phenylalaninol. Chirality 2003;15:609-614.