Introduction to chiral crystallization of achiral organic compounds: Spontaneous generation of chirality

Journal of Photochemistry and Photobiology C: Photochemistry Reviews

Volumn 6, Issue 1, 2005, Pages 7-24

  Matsuura, Teruo ^a   Koshima, Hideko ^b  

^a Ehime University ^*  (Japan)

^b EHIME UNIVERSITY   (Japan)

Author keywords

Achiral organic compounds; Cambridge structural database; Chiral crystallization; Chiral crystals; Chiral space group; Chirality generation; Enantiomorphic crystals; Optical activity; Spontaneous resolution; X ray crystallographic analysis

Indexed keywords

CRYSTALLINE MATERIALS; CRYSTALLIZATION; PHOTOCHEMICAL REACTIONS; SOLUTIONS;

ACHIRAL ORGANIC COMPOUNDS; CHIRAL CRYSTALLIZATION; CHIRAL CRYSTALS; CHIRALITY;

ORGANIC COMPOUNDS;

EID: 17644407415     PISSN: 13895567     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotochemrev.2005.02.002     Document Type: Review

References (119)

1. H. Koshima, and T. Matsuura Kokagaku (Photochemistry) 3 1996 64 65 (in Japanese)
2. H. Koshima, K. Ding, Y. Chisaka, and T. Matsuura J. Am. Chem. Soc. 118 1996 12059 12065
3. Distributed from the Cambridge Crystallographic Data Centre.
4. D. Hashizume, F. Iwasaki, H. Koshima, J.-B. Meng, Z. Wen, and T. Matsuura Proceedings of the14th International Conference on the Chemistry of the Organic Solid State Cambridge University 1999
5. H. Koshima, and T. Matsuura J. Synth. Org. Chem. (Yuki Gosei Kagaku Kyokaishi) 56 1998 268 279 466-477 (in Japanese)
6. L.F. Fieser, and M. Fieser Organic Chemistry third ed. 1956 Heath Lexington MA
7. T.M. Lowry Optical Rotatory Power 1964 Dover Publications New York p. 338
8. A. Jaques, A. Collet, and S.H. Wilen Enantiomers, Racemates and Resolutions 1981 Wiley New York pp. 14-18
9. B.S. Green, M. Lahav, and D. Rabinovich Acc. Chem. Res. 12 1979 191
10. L. Leiserowitz, and M. Weinstein Acta. Crystallogr. B31 1975 1463 1466
11. L. Addadi, and M. Lahav Pure Appl. Chem. 51 1979 1269 1284
12. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York p. 998
13. M. Hasegawa Chem. Rev. 83 1983 507 518
14. V. Ramamurthy Tetrahedron 42 1986 5753 5839
15. J.R. Scheffer, M.A. Garcia-Garibay, and O. Nalamasu A. Padwa Organic Photochemistry vol. 8 1987 Marcel Dekker New York, Basel 249 338
16. V. Ramamurthy, and K. Venkatesan Chem. Rev. 87 1987 433 481
17. K.-L. Ding, Y. Wang, Y.-J. Wu, T. Matsuura, and H. Koshima Youji Huaxue 16 1996 1 10 (in Chinese)
18. M. Sakamoto Chem. Eur. J. 3 1997 684 689
19. B.L. Feringa, and R.A. van Delden Angew. Chem. Int. Ed. Engl. 39 1999 3418 3438
20. H. Koshima F. Toda Organic Solid State Reactions 2002 Kluwer Academic Publishers Dordrecht 189 268
21. H. Koshima Y. Inoue V. Ramamurthy Chiral Photochemistry 2004 Marcel Dekker New York 485 531
22. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 John Wiley & Sons New York p. 1191
23. J.D.H. Donnay, H.M. Ondik (Eds.), Crystal Data Determinative Tables, third ed.; vol. 1, Organic Compounds, 1972; vol. 3, Organic Compounds, 1978, vol. 5, Organic Compounds, 1983; vol. 6, 1983, U.S. Department of Commerce, National Bureau of Standards, JDCPS (the Joint Committee on Powder Diffraction Standards U.S.A.).
24. J.D.H. Donnay, H.M. Ondik (Eds.), Crystal Data Determinative Tables, third ed.; vol. 1, Organic Compounds, 1972; vol. 3, Organic Compounds, 1978, vol. 5, Organic Compounds, 1983; vol. 6, 1983, U.S. Department of Commerce, National Bureau of Standards, JDCPS (the Joint Committee on Powder Diffraction Standards U.S.A.).
25. J.D.H. Donnay, H.M. Ondik (Eds.), Crystal Data Determinative Tables, third ed.; vol. 1, Organic Compounds, 1972; vol. 3, Organic Compounds, 1978, vol. 5, Organic Compounds, 1983; vol. 6, 1983, U.S. Department of Commerce, National Bureau of Standards, JDCPS (the Joint Committee on Powder Diffraction Standards U.S.A.).
26. J.D.H. Donnay, H.M. Ondik (Eds.), Crystal Data Determinative Tables, third ed.; vol. 1, Organic Compounds, 1972; vol. 3, Organic Compounds, 1978, vol. 5, Organic Compounds, 1983; vol. 6, 1983, U.S. Department of Commerce, National Bureau of Standards, JDCPS (the Joint Committee on Powder Diffraction Standards U.S.A.).
27. J.D.H. Donnay, H.M. Ondik (Eds.), Crystal Data Determinative Tables, third ed.; vol. 1, Organic Compounds, 1972; vol. 3, Organic Compounds, 1978, vol. 5, Organic Compounds, 1983; vol. 6, 1983, U.S. Department of Commerce, National Bureau of Standards, JDCPS (the Joint Committee on Powder Diffraction Standards U.S.A.).
28. L. Pasteur Ann. Chim. Phys. 24 1848 442
29. E. Havinga, Chem. Weekbl. 38 (1941) 642; Biochim. Biophys. Acta 13 (1954) 171-174.
30. E. Havinga, Chem. Weekbl. 38 (1941) 642; Biochim. Biophys. Acta 13 (1954) 171-174.
31. S.H. Wilen, A. Collet, and A. Jaques Tetrahedron 33 1977 2725 2736
32. A. Jaques, A. Collet, and S.H. Wilen Enantiomers Racemates and Resolutions 1981 Wiley New York
33. A. Jaques, M.J. Brienne, and A. Collet Chem. Rev. 80 1980 215 230
34. R.E. Pincock, and K.R. Wilson J. Am. Chem. Soc. 93 1971 1291 1292
35. R.E. Pincock, and K.R. Wilson J. Chem. Educ. 50 1973 455
36. D.J. Williams, and D. Lawton Tetrahedron Lett. 16 1975 111 114
37. A.C.D. Newman, and H.M. Powell J. Chem. Soc. 1952 3747 3751
38. J. Choi, M.D. Aggarwal, W.S. Wang, R. Metzel, and K. Bhat Crystal growth of organic materials A.S. Myerson D.A. Green P. Meenan ACS Conference Proceedings Series American Chemical Society, Washington, DC 1995 263 265
39. M. Ataka Crystallization Processes H. Otaki Wiley Series in Solution Chemistry 3 1998 Wiley New York 131
40. M. Ataka N. Hirayama Handbook for Preparation of Organic Crystals 2000 Maruzen Ltd. Tokyo 33 48 [Yukikessho Sakusei Handobokku (in Japanese)]
41. Y. Iitaka Acta Crystallogr. 13 1960 35 45
42. L.J.W. Shimon, M. Lahav, and L. Leiserowitz Nouv. J. Chem. 10 1986 723
43. A. Gavezzotti Acc. Chem. Res. 27 1994 309 314
44. J.D. Dunitz, and J. Bernstein Acc. Chem. Res. 28 1995 193 200
45. N. Blagden, and R. Davey Chem. Br. 1999 44 47
46. M.D. Aggarwal, W.S. Wang, J. Choi, K.J. Chang, A.W. Shields, B.G. Penn, and D.O. Fraser Meas. Sci. Technol. 4 1993 228 230
47. H. Koshima, E. Hayashi, T. Matsuura, K. Tanaka, F. Toda, M. Kato, and M. Kiguchi Tetrahedron Lett. 38 1997 5009 5012
48. D.K. Kondepudi, R.J. Kaufman, and N. Singh Science 250 1990 975 976
49. D.K. Kondepudi, K.L. Bullock, J.A. Digits, J.K. Hall, and J.M. Miller J. Am. Chem. Soc. 115 1993 10211 10216
50. D.K. Kondepudi, and N. Singh Chem. Phys. Lett. 217 1994 364 368
51. Private communication of Professor D.K. Kondepudi.
52. J.M. McBride, and R.L. Carter Angew. Chem. Int. Ed. Engl. 30 1991 293 295
53. H. Koshima, S.I. Khan, and M.A. Garcia-Garibay Tetrahedron: Asymmetry 9 1998 1851 1854
54. H. Koshima, S. Honke, and J. Fujita J. Org. Chem. 64 1999 3916 3921
55. H. Koshima, S. Honke, and F. Miyauchi Mol. Cryst. Liq. Cryst. 356 2001 495 502
56. J.D. Dunitz X-Ray Analysis and the Structure of Organic Molecules 1996 Verlag Helvetica Chimica Acta, VCH Basel, Weinheim, New York, Basel, Cambridge, Tokyo
57. S. Ohba, and S. Yano X-Ray Structural Analysis (X-Sen Kouzou Kaiseki) 1999 Asakura Ltd. Tokyo (in Japanese)
58. S.R. Hall, F.H. Allen, I.D. Brown, Acta Crystallogr. A47 (1991) 655-685. Also see instructions to authors of the latest issue of Acta Crystallogr. Section C and Ref. [52], pp. 152-155.
59. S.R. Hall, F.H. Allen, I.D. Brown, Acta Crystallogr. A47 (1991) 655-685. Also see instructions to authors of the latest issue of Acta Crystallogr. Section C and Ref. [52], pp. 152-155.
60. J. Kobayashi, and Y. Uesu J. Appl. Crystallogr. 16 1983 204 211
61. J. Kobayashi, K. Saito, N. Takahashi, and I. Kamiya Phys. Rev. B48 1993 10038
62. J. Kobayashi Ferroelectrics 203 1997 27 56
63. J. Kobayashi Nihon Kesshou Gakkaishi 37 1995 291 300 (in Japanese)
64. J. Kobayashi, T. Asahi, M. Ichiki, A. Oikawa, H. Suzuki, T. Watanabe, E. Fukuda, and Y. Shikinami J. Appl. Phys. 77 1995 2957 2973
65. T. Asahi, M. Nakamura, J. Kobayashi, F. Toda, and H. Miyamoto J. Am. Chem. Soc. 119 1997 3665 3669
66. H. Koshima, M. Nagano, and T. Asahi J. Am. Chem. Soc. 127 2005 2455 2463
67. Kuroda, Ph.D. thesis, The University of Tokyo, 1975.
68. R. Kuroda, and Y. Saito Bull. Chem. Soc. Jpn. 49 1976 433
69. P. Biscarini, R. Franca, and R. Kuroda Inorg. Chem. 34 1995 4618 4626
70. S.F. Mason, and R.H. Seal Mol. Phys. 31 1976 755
71. JASCO Report, 3 (1969) 10.
72. F. Toda, H. Miyamoto, S. Kikuchi, R. Kuroda, and F. Nagami J. Am. Chem. Soc. 118 1996 11315 11316
73. I. Azumaya, K. Yamaguchi, I. Okamoto, H. Kagechika, and K. Shudo J. Am. Chem. Soc. 117 1995 9083 9084
74. M. Sakamoto, M. Takahashi, S. Morizumi, K. Yamaguchi, T. Fujita, and S. Watanabe J. Am. Chem. Soc. 118 1996 8138 8139
75. H. Koshima, T. Nakagawa, T. Matsuura, H. Miyamoto, and F. Toda J. Org. Chem. 62 1997 6322 6325
76. A.S. Meyerson Handbook of Industrial Crystallization 2000 Butterworth-Heinemann London 79
77. L.J.W. Shimon, M. Vaida, L. Addadi, M. Lahav, and L. Leiserowitz J.B. Garbarczyk D.W. Jones Organic Crystal Chemistry 1991 Oxford University Press New York 72
78. R. Docherty A.S. Myerson D.A. Green P. Meenan Crystal Growth of Organic Materials ACS Conference Proceedings Series, American Chemical Society, Washington, DC 1996 2
79. S. Momonaga, S. Hennings, and J. Ulrich A.S. Myerson D.A. Green P. Meenan Crystal Growth of Organic Materials ACS Conference Proceedings Series, American Chemical Society, Washington, DC 1996 200 208
80. R.F.P. Grimbergen, and P. Bennema A.S. Myerson D.A. Green P. Meenan Crystal Growth of Organic Materials ACS Conference Proceedings Series, American Chemical Society, Washington, DC 1996 28 35
81. P. Hartman, and W.G. Perdock Acta Cryst. 1955 49 52
82. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York p. 600
83. F. Toda, K. Tanaka, and R. Kuroda Chem. Commun. 1997 1227 1228
84. E.L. Eliel, S.H. Wilen, and L.N. Mander Stereochemistry of Organic Compounds 1994 Wiley New York p. 1012
85. E.B. Fleischer, N. Sung, and S. Hawkinson J. Phys. Chem. 72 1968 4311 4312
86. H. Koshima Kokagaku (Photochemistry) 3 1996 64 65 (in Japanese), and unpublished data
87. P.T. Clarke, and J.M. Spink Acta Crystallogr. B25 1969 162
88. P.R. Chowdhury Acta Crystallogr. B29 1973 1362 1364
89. H. Koshima, unpublished data.
90. H. Gillier-Pandraud, Bull. Soc. Chim. Fr. (1967) 1988.
91. C.Z. Scheringer Kristallogr. 119 1963 273
92. A.L. Macdonald, and J. Trotter J. Chem. Soc. Perkin II 1973 476 480
93. E. Harnik, F.H. Herbstein, G.M.J. Schmidt, and F.L. Hirshfeld J. Chem. Soc. 1954 3288 3294
94. F.H. Herbstein, and G.M.J. Schmidt J. Chem. Soc. 1954 3302 3319
95. A.T. Vincent, and P.J. Wheatley J. Chem. Soc. Dalton 1972 617 622
96. A. Mostad, C. Rømnting, and L. Tressum Acta Chem. Scand. B29 1975 171
97. M. Cesario, J. Gulihero, C. Pascard, A. Collet, and J. Jacques Nouv. J. Chem. 2 1978 343
98. Y. Schouwstra Acta Crystallogr. B29 1973 1636 1641
99. F. Baert, thesis no. 149, Lillie, 1976.
100. J.D. Wright, Molecular Crystals, Cambridge University Press, 1987 (Bunnshi Kessho (Japanese translation), Kagaku Dojin, Kyoto, 1991).
101. J.D. Wright, Molecular Crystals, Cambridge University Press, 1987 (Bunnshi Kessho (Japanese translation), Kagaku Dojin, Kyoto, 1991).
102. G.R. Desiraju Crystal Engineering: The Design of Organic Solids 1989 Elsevier Amsterdam
103. J.B. Garbarczyk, and D.W. Jones Organic Crystal Chemistry 1991 Oxford University Press
104. M. Kimura, and F. Toda Yuki Kotai Kagaku (Organic Solid-State Chemistry) 1993 Sankyo Publ. Ltd. Tokyo (in Japanese)
105. Proceedings of the International Conference of the Chemistry of the Organic Solid State (ICCOSS): ICCOSS XI, Mol. Cryst. Liq. Cryst. 240, 242, 248 (1994); ICCOSS XII, Mol. Cryst. Liq. Cryst. 276-279 (1996); ICCOSS XIII, Mol. Cryst. Liq. Cryst. 313 (1996); ICCOSS XIV, Mol. Cryst. Liq. Cryst. 356 (1999).
106. Proceedings of the International Conference of the Chemistry of the Organic Solid State (ICCOSS): ICCOSS XI, Mol. Cryst. Liq. Cryst. 240, 242, 248 (1994); ICCOSS XII, Mol. Cryst. Liq. Cryst. 276-279 (1996); ICCOSS XIII, Mol. Cryst. Liq. Cryst. 313 (1996); ICCOSS XIV, Mol. Cryst. Liq. Cryst. 356 (1999).
107. Proceedings of the International Conference of the Chemistry of the Organic Solid State (ICCOSS): ICCOSS XI, Mol. Cryst. Liq. Cryst. 240, 242, 248 (1994); ICCOSS XII, Mol. Cryst. Liq. Cryst. 276-279 (1996); ICCOSS XIII, Mol. Cryst. Liq. Cryst. 313 (1996); ICCOSS XIV, Mol. Cryst. Liq. Cryst. 356 (1999).
108. Proceedings of the International Conference of the Chemistry of the Organic Solid State (ICCOSS): ICCOSS XI, Mol. Cryst. Liq. Cryst. 240, 242, 248 (1994); ICCOSS XII, Mol. Cryst. Liq. Cryst. 276-279 (1996); ICCOSS XIII, Mol. Cryst. Liq. Cryst. 313 (1996); ICCOSS XIV, Mol. Cryst. Liq. Cryst. 356 (1999).
109. A. Gavezzotti Acc. Chem. Res. 27 1994 309 314
110. L. Leiserowitz, and M. Weinstein Acta Crystallogr. B31 1975 1463 1466
111. L. Leiserowitz, and G.M.J. Schmidt J. Chem. Soc. A 1969 2372 2382
112. L. Leiserowitz Acta Crystallogr. B32 1976 775 802
113. B.S. Green, M. Lahav, and D. Rabinovich Acc. Chem. Res. 12 1979 191 197
114. H. Koshima, and T. Matsuura Mol. Cryst. Liq. Cryst. 313 1998 65 74
115. H. Koshima, and T. Matsuura A.S. Myerson D.A. Green P. Meenan Crystal Growth of Organic Materials ACS Conference Proceedings Series, American Chemical Society, Washington, DC 1996 239 245
116. A. Collet, and J. Jacques Bull. Soc. Chim. Fr. 1972 3700
117. A. Collet, M.-J. Brienne, and J. Jacques Bull. Soc. Chim. Fr. 1972 127 142
118. H. Koshima, K. Ding, Y. Chisaka, T. Matsuura, I. Miyahara, and K. Hirotsu J. Am. Chem. Soc. 119 1997 10317 10324
119. B.S. Green, unpublished work cited in [103].