Crystallization-induced diastereomer transformations

Chemical Reviews

Volumn 106, Issue 7, 2006, Pages 2711-2733

  Brands, Karel M Jos ^a   Davies, Antony J ^a  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CRYSTALLIZATION; HYDROGEN BONDS; MOLECULAR STRUCTURE; SUBSTITUTION REACTIONS;

COVALENT DIASTEREOMERS; CRYSTALLIZATION-INDUCED DIASTEREOMER TRANSFORMATIONS; PROTON TRANSFER;

PHASE TRANSITIONS;

AMINO ACID; ORGANOMETALLIC COMPOUND;

CHEMICAL STRUCTURE; CHEMISTRY; CRYSTALLIZATION; METHODOLOGY; ORGANIC CHEMISTRY; REVIEW; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CHEMISTRY, ORGANIC; CRYSTALLIZATION; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM;

EID: 33746874836     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0406864     Document Type: Review

References (210)

1. Selected references: (a) Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
2. (b) In Preparative Chromatography of Fine Chemicals and Pharmaceutical Agents; Schmidt-Traub, H., Ed.; Wiley-VCH: Weinheim, Germany, 2005.
3. (c) Welch, C. J. Chiral Chromatography in Support of Pharmaceutical Process Research. In Preparative Enantioselective Chromatography; Cox, G., Ed.; Blackwell: London, 2005; pp 1-18.
4. Chen, C.-K.; Singh, A. K. Org. Process Res. Dev. 2001, 5, 508.
5. Anderson, N. G. Org. Process Res. Dev. 2004, 8, 260.
6. Jamison, M. M. Trans. Faraday Soc. 1945, 41, 696.
7. Harris M. M. The Study of Optically Labile Compounds. In Progress in Stereochemistry; Klyne, W., de la Marc, P. B. D., Eds.; Butterworth: London, 1958; Vol. 2, pp 157-195.
8. Sheldon, R. A. Chirotechnology; Marcel Dekker Inc.: New York, 1993; pp 197-201.
9. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Krieger Publishing: Malabar, FL, 1994; pp 369-377.
10. Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience: New York, 1994; pp 364-374.
11. Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 25, 447.
12. Arai, K. Yuki Gosei Kagaku Kyokaishi 1986, 44, 486.
13. Anderson, N. G. Org. Process Res. Dev. 2005, 9, 800.
14. Selected examples: (a) Mioskowski, C.; Solladie, G. Tetrahedron 1980, 36, 227.
15. (b) Feringa, B. L.; de Jong, J. C. J. Org. Chem. 1988, 53, 1125.
16. (c) Solladié, G.; Lohse, O. Tetrahedron: Asymmetry 1993, 4, 1547.
17. (d) Moseley, J. D.; Williams, B. J.; Owen, S. N.; Verrier, H. M. Tetrahedron: Asymmetry 1996, 7, 3351.
18. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Krieger Publishing: Malabar, FL, 1994; pp 32-131.
19. Kinbara, K.; Saigo, K. Chiral Discrimination during Crystallization. In Topics in Stereochemistry; Denmark, S. E., Ed.; Wiley: New York, 2003.; Vol. 23, pp 207-265.
20. Kuhn, R.; Jochims, J. C. Justus Liebigs Ann. Chem. 1961, 641, 143.
21. Hassan, N. A.; Bayer, E.; Jochims, J. C. J. Chem. Soc., Perkin Trans. 1 1998, 3747.
22. In most examples of this phenomenon the system contains two components. However, in principle, the system can have any number of equilibrating components. Mathematically the treatment obviously becomes more complex, but the conclusions remain essentially the same.
23. Kuhn, R. Ber. Dtsch. Chem. Ges. 1932, 65, 49.
24. Dimroth, O. Justus Liebigs Ann. Chem. 1910, 377, 127.
25. Shiraiwa, T.; Sakata, S.; Fujishima, K.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 191.
26. Some selected references: (a) Havinga, E. Biochim. Biophys. Acta 1954, 13, 171.
27. (b) Black, S. N.; Williams, L. J.; Davey, R. J.; Moffatt, F.; Jones, R. V. H.; McEwan, D. M.; Sadler, D. E. Tetrahedron 1989, 45, 2677.
28. (c) Okada, Y.; Takebayashi, T.; Aoki, S.; Sato, S. Heterocycles 1990, 31, 1923.
29. (d) Küenburg, B.; Czollner, L.; Fröhlich, J.; Jordis, U. Org. Process Res. Dev. 1999, 3, 425.
30. (e) Kostyanovsky, R. G.; Kostyanovsky, V. R.; Kadorkina, G. K.; Lyssenko, K. A. Mendeleev Commun. 2001, 1.
31. (f) Kostyanovsky, R. G.; Kostyanovsky, V. R.; Kadorkina, G. K.; Lyssenko, K. A. Mendeleev Commun. 2003, 111.
32. (g) Sifniades, S. L-Lysine via Asymmetric Transformation of α-Amino-ε-Caprolactam. In Chirality in Industry; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: Chichester, 1992; Chapter 3.
33. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates and Resolutions; Krieger Publishing: Malabar, FL, 1994; p 81.
34. (a) Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475.
35. (b) Pellissier, H. Tetrahedron 2003, 59, 8291.
36. Beak et al. recently coined the term "Dynamic Thermodynamic Resolution" (Acc. Chem. Res. 2000, 33, 715). We do not believe that the crystallization-induced processes described in this review are accurately described by this term.
37. Leuchs, H.; Wutke, J. Ber. Dtsch. Chem. Ges. 1913, 46, 2420.
38. Leuchs, H. Ber. Dtsch. Chem. Ges. 1921, 54, 830.
39. Davidson, E. M.; Turner, E. E. J. Chem. Soc. 1945, 843.
40. Ashley, W. C.; Shriner, R. L. J. Am. Chem. Soc. 1932, 54, 4410.
41. Hargreaves, M. K.; Khan, M. A. J. Chem. Soc., Perkin Trans. 2 1973, 1204.
42. Sohda, T.; Mizuno, K.; Kawamatsu, Y. Chem. Pharm. Bull. 1984, 32, 4460.
43. Kim, K. S.; Sack, J. S.; Tokarski, J. S.; Qian, L.; Chao, S. T.; Leith, L.; Kelly, Y. F.; Misra, R. N.; Hunt, J. T.; Kimball, S. D.; Humphreys, W. G.; Wautlet, B. S.; Mulheron, J. G.; Webster, K. R. J. Med. Chem. 2000, 43, 4126.
44. Ashcroft, C. P.; Challenger, S.; Clifford, D.; Derrick, A. M.; Hajikarimian, Y.; Slucock, K.; Silk, T. V.; Thomson, N. M.; Williams, J. R. Org. Process Res. Dev. 2005, 9, 663.
45. Mills, W. H.; Bain, A. M. J. Chem. Soc. 1911, 1866.
46. Mills, W. H.; Bain, A. M. J. Chem. Soc. 1914, 64.
47. Campbell, I. G. M. J. Chem. Soc. 1947, 4.
48. Rây, P.; Dutt, N. K. J. Indian Chem. Soc. 1941, 18, 289.
49. Mills, W. H.; Elliot, K. A. C. J. Chem. Soc. 1928, 1291.
50. Adams, R.; Sundstrom, K. V. Y. J. Am. Chem. Soc. 1954, 76, 5474.
51. Adams, R.; Blomstrom, D. C.; Sundstrom, K. V. Y. J. Am. Chem. Soc. 1954, 76, 5478.
52. Adams, R.; Brower, K. R.. J. Am. Chem. Soc. 1956, 78, 663.
53. Yuan, H. C.; Adams, R. J. Am. Chem. Soc. 1932, 54, 2966.
54. Adams, R.; Kornblum, N. J. Am. Chem. Soc. 1941, 63, 188.
55. Stoughton, R. W.; Adams, R. J. Am. Chem. Soc. 1932, 54, 4426.
56. Yuan, H. C.; Adams, R. J. Am. Chem. Soc. 1932, 54, 4434.
57. Searle, N. E.; Adams, R. J. Am. Chem. Soc. 1933, 55, 1649.
58. Kuhn, R.; Albrecht, O. Justus Liebigs Ann. Chem. 1927, 455, 272.
59. Jamison, M. M.; Turner, E. E. J. Chem. Soc. 1942, 437.
60. Corbellini, A.; Angeletti, M. Matematiche e Naturali, Rendiconti 1932, 15, 968.
61. Lesslie, M. S.; Mayer, U. J. H. J. Chem. Soc. 1961, 611.
62. Mislow, K.; Hyden, S.; Schaefer. H. Tetrahedron Lett. 1961, 2, 410.
63. Mislow, K.; Hyden, S.; Schaefer, H. J. Am. Chem. Soc. 1962, 84, 1449.
64. Warnhoff, E. W.; Reynolds-Warnhoff, P. Can. J. Chem. 1973, 51, 2338.
65. Almqvist, A.; Hakansson, R. Chem. Scr. 1977, 11, 180.
66. Meisenheimer, J.; Beisswenger, O Ber. Dtsch. Chem. Ges. 1932, 65, 32.
67. Hall, D. M.; Ridgwell, S.; Turner, E. E. J. Chem. Soc. 1954, 2498.
68. Jamison, M. M.; Turner, E. E. J. Chem. Soc. 1938, 1646.
69. Jamison, M. M.; Turner, E. E. J. Chem. Soc. 1940, 264.
70. Buchanan, C.; Graham, S. H. J. Chem. Soc. 1950, 500.
71. Brussee, J.; Groenendijk, J. L. G.; te Koppele, J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313.
72. It was not reported in this study if, and by how much, the decomplexed binaphthol was upgraded in its crystallization.
73. Smrcina, M.; Lorenc, M.; Hanus, V.; Sedmera, P.; Kocovsky, P. J. Org. Chem. 1992, 57, 1917.
74. Tsubaki, K.; Miura, M.; Morikawa, H.; Hiroyuki, T.; Kawabata, T.; Furuta, T.; Kiyoshi, T.; Fuji, K. J. Am. Chem. Soc. 2003, 125, 16200.
75. Adams, R.; Gross, W. J. J. Am. Chem. Soc. 1942, 64, 1786.
76. Newman, M. S.; Hussey, A. S. J. Am. Chem. Soc. 1947, 69, 3023.
77. Coogan, M. P.; Smart E.; Hibbs, D. E. Chem. Commun, 1999, 1991.
78. Wilen, S. H.; Qi, J. Z.; Williard, P. G. J. Org. Chem. 1991, 56, 485.
79. Konoike, T.; Matsumura, K.; Yorifuji, T.; Shinomoto, S.; Ide, Y.; Ohya, T. J. Org. Chem. 2002, 67, 7741.
80. (a) Hoppe, D.; Zschage, O. Angew. Chem., Int. Ed. Engl. 1989, 28, 69.
81. (b) Zschage, O.; Hoppe, D. Tetrahedron 1992, 48, 5657.
82. Toda, F.; Tanaka, K. Chem. Lett. 1983, 661.
83. Openshaw, H. T.; Whittaker, N. J. Chem. Soc. 1963, 1461.
84. Blaskó, G.; Knight, H.; Honty, K.; Szántay, C. Liebigs Ann. Chem. 1986, 655.
85. Clark, R. D.; Kern, J. R.; Kurz, L. J.; Nelson, J. T. Heterocycles 1990, 31, 353.
86. (a) Busch, F. R.; Chiu, C. K.-F.; Meltz, C. N.; Post, R. J.; Rose, P. R. Process for Preparing Growth Hormone Secretagogues. Eur. Pat. Appl. EP 1031575 A1, 2000; Chem. Abstr. 2000, 133, 193497.
87. (b) Busch, F. R.; Chiu, C. K.-F.; Meltz, C. N.; Post, R. J.; Rose, P. R. Process for Preparation of Pyrazolopyridine Tartrates. Eur. Pat. Appl. EP 1449842 A1, 2004; Chem. Abstr. 2004, 141, 207204.
88. (c) See also: Zawistoski, M. P.; Lefker, B. A.; Inthavongsay, J. K.; Carpino, P. A.; Mangano, F. M.; Rose, C. R.; Wright, A. S. Abstracts of Papers, Part 2, 216th National Meeting of the American Chemical Society, Boston, MA, Aug 23-27, 1998; American Chemical Society: Washington, DC, 1998.
89. Mueller-Boetticher, H.; Bressler, G.-R.; Kreye, P. Enantiomer Separation of Piperidone Derivatives with Simultaneous In-situ Racemization of the Unwanted Enantiomer. PCT Intl. Appl. WO 2001096306 A1, 2001; Chem. Abstr. 2004, 136, 37523.
90. Soloshonok, V. A.; Kukhar, V. P.; Galushko, S. V.; Svistunova, N. Y.; Avilov, D. V.; Kuz'mina, N. A.; Raevski, N. I.; Struchkov, Y. T.; Pysarevsky, A. P.; Belokon, Y. N. J. Chem. Soc., Perkin Trans. 1 1993, 3143.
91. Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1994, 59, 5463.
92. Chaplin, D. A.; Johnson, N. B.; Paul, J. M.; Potter, G. A. Tetrahedron Lett. 1998, 39, 6777.
93. Chen, J. G.; Zhu, J.; Skonezny, P. M.; Rosso, V.; Venit, J. J. Org. Lett. 2004, 6, 3233.
94. Kiau, S.; Discordia, R. P.; Madding, G.; Okuniewicz, F. J.; Rosso, V.; Venit, J. J. J. Org. Chem. 2004, 69, 4256.
95. Clark, J. C.; Phillipps, G. H.; Steer, M. R.; Stephenson, L.; Cooksey, A. R. J. Chem. Soc., Perkin Trans. 1 1976, 471.
96. Clark, J. C.; Elks, J. Process for the Preparation of Optically Active α-Aminoacid Esters. Ger. Offen. DE 2309180, 1973; Chem. Abstr. 1973, 79, 126791.
97. Yamada, S.; Hongo, C.; Yoshioka, R.; Chibata, I. J. Org. Chem. 1983, 48, 843.
98. Clark, J. C.; Phillipps, G. H.; Steer, M. R. J. Chem. Soc., Perkin Trans. 1 1976, 475.
99. Lopata, A.; Faigl, F.; Fogassy, E.; Darvas, F. J. Chem. Res., Synop. 1984, 322.
100. Grigg, R.; Gunaratne, H, Q, N. Tetrahedron Lett. 1983, 24, 4457.
101. Stamicarbon, B. V. Process for the Preparation of Optically Active Phenyl Glycine Amide. UK 1 560 906, 1976.
102. Boesten, W. H. Process for the Preparation of Optically Active Amino Acid Amide. Eur. Pat. Appl. EP 442584 A1, 1991; Chem. Abstr. 1991, 116, 42062.
103. Matthews, G. J. Resolution-Racemization of α-Amino-α-Phenylacetonitrile. U.S. Patent 3,808,254, Apr 30, 1974.
104. Shiraiwa, T.; Sakata, S.; Natsuyama, H.; Fujishima, K.; Miyazaki, H.; Kubo, S.; Nitta, T.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1992, 65, 965.
105. Shiraiwa, T.; Sakata, S.; Kurokawa, H. Chem. Express 1988, 3, 415.
106. Shiraiwa, T.; Chatani, T.; Matsushita, T.; Kurokawa, H. Technol. Rep. Kansai Univ. 1985, 26, 103.
107. Bhattacharya, A,; Araullo-McAdams, C.; Meier, M. B. Synth. Commun. 1994, 24, 2449.
108. Jacewicz, V. W. Process for the Racemization of an α-Amino Acid. Eur. Pat. Appl. EP 173921 A1, 1986; Chem. Abstr. 1986, 105, 60942.
109. Yoshioka, R.; Ohtsuki, O.; Senuma, M.; Tosa, T. Chem. Pharm. Bull. 1989, 37, 883.
110. Chibata, I.; Yamada, S.; Hongo, C.; Yoshioka, R. p-Hydroxyphenylglycine α-phenylethanesulfonate. Process for Production Thereof and Utilization Thereof in Resolution of p-Hydroxyphenylglycine. Eur. Pat. Appl. EP 75318 A2, 1983; Chem. Abstr. 1983, 99, 105702.
111. Yoshioka, R.; Tohyama, M.; Ohtsuki, O.; Yamada, S.; Chibata, I. Bull. Chem. Soc. Jpn. 1987, 60, 649.
112. Yoshioka, R.; Tohyama, M.; Yamada, S.; Ohtsuki, O.; Chibata, I. Bull. Chem. Soc. Jpn. 1987, 60, 4321.
113. Maryanoff, C. A.; Scott, L.; Shah, R. D.; Villani, F. J., Jr. Tetrahedron: Asymmetry 1998, 9, 3247.
114. Shiraiwa, T.; Shinjo, K.; Kurokawa, H. Chem. Lett. 1989, 1413.
115. Shiraiwa, T.; Shinjo, K.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3251.
116. Dyer, U. C.; Lock, C. J.; Woods, M. Racemization and Asymmetric Transformation Processes Used in the Manufacture of Levobupivacaine and Analogues Thereof. PCT Intl. Appl. WO 9609290 A1, 1996; Chem. Abstr. 1996, 125, 86510.
117. Lock, C. J. Asymmetric Transformation of Pipecolic Acid, a Precursor of Levobupivacaine and Analogues Thereof. PCT Intl. Appl. WO 9611185 A1, 1996; Chem. Abstr. 1996, 125, 115134.
118. Shiraiwa, T.; Furukawa, T.; Tsuchida, S.; Sakata, M.; Sunami, M.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3729.
119. Shiraiwa, T.; Sjinjo, K.; Masui, Y.; Ohta, A.; Natsuyama, H.; Miyazaki, H.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1991, 64, 3741.
120. Shiraiwa, T.; Kataoka, K.; Kurokawa, H. Chem. Lett. 1987, 2041.
121. Shiraiwa, T.; Kataoka, K.; Sakata, S.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1989, 62, 109.
122. Miyazaki, H.; Ohta, A.; Kawakatsu, N.; Waki, Y.; Gogun, Y.; Shiraiwa, T.; Kurokawa, H. Bull. Chem. Soc. Jpn. 1993, 66, 536.
123. Shiraiwa, T.; Tadokoro, K.; Ishikawa, J.; Tanaka, H.; Masaki, T.; Kurokawa, H. Biosci. Biotechnol. Biochem. 2000, 64, 341.
124. Knorr, H.; Schlegel, G.; Stark, H. Process for the Preparation of L-Homoalanine-4-yl-(methyl)phosphinic Acid and its Salts via Resolution. Ger. Offen. DE 4407197 A1, 1995; Chem. Abstr. 1995, 124, 30406.
125. Reider, P. J.; Davis, P.; Hughes, D. L.; Grabowski, E. J. J. J. Org. Chem. 1987, 52, 955.
126. Boyer, S. K.; Pfund, R. A.; Portmann, R. E.; Sedelmeier, G. H.; Wetter, H. F. Helv. Chim. Acta 1988, 71, 337.
127. Armstrong, J. D., III; Eng, K. K.; Keller, J. L.; Purick, R. M.; Hartner, F. W., Jr.; Choi, W.-B.; Askin, D.; Volante, R. P. Tetrahedron Lett. 1994, 35, 3239.
128. Shi, Y.-J.; Wells, K. M.; Pye, P. J.; Choi, W.-B.; Churchill, H. R. O.; Lynch, J. E.; Maliakal, A.; Rossen, K.; Reider, P. J.; Sager, J. W.; Volante, R. P. Tetrahedron 1999, 55, 909.
129. Singh, J.; Kronenthal, D. R.; Schwinden, M.; Godfrey, J. D.; Fox, R.; Vawter, E. J.; Zhang, B.; Kissick, T. P.; Patel, B.; Mneimne, O.; Humora, M.; Papaioannou, C. G.; Szymanski, W.; Wong, M. K. Y.; Chen, C. K.; Heikes, J. E.; DiMarco, J. D.; Qiu, J.; Deshpande, R. P.; Gougoutas, J. Z.; Mueller, R. H. Org. Lett. 2003, 5, 3155.
130. Macdonald, S. J. F.; Clarke, G. D. E.; Dowle, M. D.; Harrison, L. A.; Hodgson, S. T.; Inglis, G. G. A.; Johnson, M. R.; Shah, P.; Upton, R. J.; Walls, S. B. J. Org. Chem. 1999, 64, 5166.
131. Barrett, R.; Caine, D. M.; Cardwell, K. S.; Cooke, J. W. B.; Lawrence, R. M.; Scott, P.; Sjolin, Å. Tetrahedron: Asymmetry 2003, 14, 3627.
132. Colson, P.-J.; Przybyla, C. A.; Wise, B. E.; Babiak, K. A.; Seaney, L. M.; Korte, D. E. Tetrahedron: Asymmetry 1998, 9, 2587.
133. Riedner, J.; Vogel, P. Tetrahedron: Asymmetry 2004, 15, 2657.
134. Alabaster, R. J.; Gibson, A. W.; Johnson, S. A.; Edwards, J. S.; Cottrell, I. F. Tetrahedron: Asymmetry 1997, 8, 447.
135. Aelterman, W.; Lang, Y.; Willemsens, B.; Vervest, I.; Leurs, S.; De Knaep, F. Org. Process Res. Dev. 2001, 5, 467.
136. Yang, H.; Qiu, G.-F.; Feng, X.-C.; He, J.-S.; Hu, X.-M. Chem. Res. Chin. Univ. 2002, 18, 409.
137. Negi, S.; Matsukura, M.; Mizuno, M.; Miyake, K.; Minami, N. Synthesis 1996, 991.
138. Dubrunfaut, A. P. C. R. Acad. Sci., Paris 1846, 23, 38.
139. Pigman, W. The Carbohydrates; Academic: New York, 1957; p 92.
140. Hagmann, W. K. Synth. Commun. 1986, 16, 437.
141. (a) Cannata, V.; Tamerlani, G. A New Process for the Optical Resolution of Racemic Mixtures of α-Naphtylpropionic Acids. Eur. Pat. Appl. EP 143371 A1, 1985; Chem. Abstr. 1985, 103, 215015.
142. (b) Cannata, V.; Tamerlani, G. A New Process for the Optical Resolution of Racemic Mixtures of α-Naphtylpropionic Acids. Eur. Pat. Appl. EP 182279 A1, 1986; Chem. Abstr. 1986, 1053, 78693.
143. Lopez, F. J.; Ferriño, S. A.; Reyes, M. S.; Román, R. Tetrahedron: Asymmetry 1997, 8, 2497.
144. Pozzoli, C.; Castaldi, G. Process for the Preparation of the Enantiomers of 2-(2-Fluoro-4-biphenyl)propionic Acid. U.S. Patent 5,840,964, Nov 24, 1998.
145. Giordano, C.; Cavicchioli, S.; Villa, M. J. Org. Chem, 1991, 56, 6114.
146. Lee, S.-K.; Lee, S. Y.; Park, Y. S. Synlett 2001, 1941.
147. Košmrlj, J.; Weigel, L. O.; Evans, D. A.; Downey, W. C.; Wu, J. J. Am. Chem. Soc. 2003, 125, 3208.
148. Cooper, J.; Humber, D. C.; Long, A. G. Synth. Commun. 1986, 16, 1469.
149. Kemperman, G. J.; Zhu, J.; Klunder, A. J. H.; Zwanenburg, B. Org. Lett. 2000, 2, 2829.
150. Stock, H. T.; Turner, N. J. Tetrahedron Lett. 1996, 37, 6575.
151. Flores-Parra, A.; Gutiérrez-Avella, D. M.; Guzmán-Vásquez, Y. J.; Ariza-Castolo, A.; Contreras, R. J. Org. Chem. 1992, 57, 6067.
152. Shieh, W.-C.; Carlson, J. A.; Zaunius, G. M. J. Org. Chem. 1997, 62, 8271.
153. Zhao, M. M.; McNamara, J. M.; Ho, G.-J.; Emerson, K. M.; Song, Z. J.; Tschaen, D. M.; Brands, K. M. J.; Dolling, U.-H.; Grabowski, E. J. J,; Reider, P. J. J. Org. Chem. 2002, 67, 6743.
154. Pye, P. J.; Rossen, K.; Weissman, S. A.; Maliakal, A.; Reamer, R. A.; Ball, R.; Tsou, N. N.; Volante, R. P.; Reider, P. J. Chem. - Eur. J. 2002, 8, 1372.
155. Brands, K. M. J.; Payack, J. F.; Rosen, J. D.; Nelson, T. D.; Candelario, A.; Huffman, M. A.; Zhao, M. M.; Li, J.; Craig, B.; Song, Z. J.; Tschaen, D. M.; Hansen, K.; Devine, P. N.; Pye, P. J.; Rossen, K.; Dormer, P. G.; Reamer, R. A.; Welch, C. J.; Mathre, D. J.; Tsou, N. N.; McNamara, J. M.; Reider, P. J. J. Am. Chem. Soc. 2003, 125, 2129.
156. Solubility measurements were carried out in the absence of base to prevent equilibration.
157. Silverberg, L. J.; Kelly, S.; Vemishetti, P.; Vipond, D. H.; Gibson, F. S.; Harrison, B.; Spector, R.; Dillon, J. L. Org. Lett. 2000, 2, 3281.
158. Silverberg, L. J.; Dillon, J. L.; Vemishetti, P.; Sleezer, P. D.; Discordia, R. P.; Hartung, K. B. Org. Process Res. Dev. 2000, 4, 34.
159. (a) Komatsu, H.; Awano, H. J. Org. Chem. 2002, 67, 5419.
160. (b) Komatsu, H.; Oikawa, T.; Ishibashi, H. J. Org. Synth. Chem., Jpn. 2005, 63, 594.
161. Napolitano, E.; Farina, V. Tetrahedron Lett. 2001, 42, 3231.
162. Eriksson, M.; Farina, V.; Kapadia, S.; Napolitano, E.; Yee, N. K. Synthesis of Cell Adhesion Inhibitors via Crystallization-Driven Dynamic Transformations. In Chemical Process Research; ACS Symposium Series 870; American Chemical Society: Washington, DC, 2004; pp 23-38.
163. Buckley, B. R.; Bulman Page, P. C.; Heaney, H.; Sampler, E. P.; Carley, S.; Brocke, C.; Brimble, M. A. Tetrahedron 2005, 61, 5876.
164. Brands, K. M. J.; Brewer, S. E.; Davies, A. J.; Dolling, U. H.; Hammond, D. C.; Lieberman, D. R.; Scott, J. P. Stereoselective Synthesis of cis-3-[4,4-(Chlorophenyl)sulfonyl-4-(2,5-difluorophenyl) cyclohexyl]propanoic Acid or its Alkali Metal Salts. PCT Intl. Appl. WO 2005080309, 2005; Chem. Abstr. 2005, 143, 266674.
165. The solubility in methanesulfonic acid could not be determined as this led to equilibration.
166. Rapoport, H.; Lavigne, J. B. J. Am. Chem. Soc. 1956, 78, 2455.
167. Ates, A.; Curran, D. P. J. Am. Chem. Soc. 2001, 123, 5130.
168. Mann, E.; Montero, A.; Maestro, M. A.; Herradón, B. Helv. Chim. Acta 2002, 85, 3624.
169. Herradón, B.; Montero, A.; Mann, E.; Maestro, M. A. Cryst. Eng. Commun. 2004, 6, 512.
170. Kanomata, N.; Ochiai, Y. Tetrahedron Lett. 2001, 42, 1045.
171. Lucci, R. Preparation of 13-cis-Retinoic Acid. US Patent 4,556,518, Dec 3, 1985.
172. Oda, Y.; Ikeda, T.; Tada, K. Synth. Commun. 1994, 24, 2195.
173. Cimarelli, C.; Palmieri, G.; Volpini, E. Tetrahedron 2001, 57, 6089.
174. Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org. Chem. 2001, 66, 4759.
175. Kuhn, R.; Jochims, J. C. Justus Liebigs Ann. Chem. 1961, 641, 143.
176. Wenges, K.; Gries, K.; Stemmle, B.; Schrank, W. Chem. Ber. 1977, 110, 2098.
177. Martell, J. The Development and Manufacture of Pyrethroid Insecticides. In Chirality in Industry; Collins, A. N., Sheldrake, G. N., Crosby, J., Eds.; Wiley: Chichester, 1992; Chapter 4.
178. Boesten, W. H. J.; Seerden, J.-P, G.; De Lange, B.; Dielemans, H. J. A.; Elsenberg, H. L. M.; Kaptein, B.; Moody, H. M.; Kellogg, R. M.; Broxterman, Q. B. Org. Lett. 2001, 3, 1121.
179. Moher, E. D. Synthesis Studies on a Conformationally Restricted Glutamic Acid Analog. Presentation at the 21st SCI Process Development Symposium, Cambridge, U.K., Dec 2003.
180. See also: Moher, E. D.; Monn, J. A.; Pedregal-Tercero, C. Prodrugs of Excitatory Amino Acids. PCT Intl. Appl. WO 2003104217 A2, 2003; Chem. Abstr. 2003, 140, 42463.
181. Urbach, H.; Henning, R. Tetrahedron Lett. 1984, 25, 1143.
182. Jacubec, P.; Berkeš, D.; Považanec, F. Tetrahedron Lett. 2004, 45, 4755.
183. Berkeš, D.; Kolarović, A.; Baran, P. J. Mol. Struct. 2004, 697, 101.
184. Kolarovič, A.; Berkeš, D.; Baran, P.; Povžanec, F. Tetrahedron Lett. 2005, 46, 975.
185. Berkeš, D.; Kolarovč, A.; Manduch, R.; Baran, P.; Považanec, F. Tetrahedron: Asymmetry 2005, 16, 1927.
186. Kolarovič, A.; Berkeš, D.; Baran, P.; Povazanec, F. Tetrahedron Lett. 2001, 42, 2579.
187. 1F Agonists. PCT Intl. Appl. WO 2004094380 A1, 2004; Chem Abstr. 2004, 141, 395422.
188. Node, M.; Nishide, K.; Fujiwara, T.; Ichihashi, S. Chem. Commun. 1998, 2363.
189. Guidi, A.; Theurillat-Moritz, V.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 3153.
190. Sevin, A.-F.; Vogel, P. J. Org. Chem. 1994, 59, 5920.
191. Theurillat-Moritz, V.; Vogel, P. Tetrahedron: Asymmetry 1996, 7, 3163.
192. Bucourt, R.; Nédélec, J.-C.; Gasc, J.-C.; Weill-Raynal, J. Bull. Soc. Chim. Fr. 1967, 561.
193. Noyori, R.; Uchiyama, M.; Nobori, T.; Hirose, M.; Hayakawa, Y. Aust. J. Chem. 1992, 45, 205.
194. Caddick, S.; Jenkins, K. Tetrahedron Lett. 1996, 37, 1301.
195. Pope, W. J.; Peachey, S. J. Proc. Chem. Soc. 1900, 16, 42.
196. Klebe, J. F.; Finkbeiner, H. J. Am. Chem. Soc. 1968, 90, 7255.
197. Trankler, K. A.; Wyman, D. S.; Corey, J. Y.; Katz, E. E.; Rath, N. P. Organometallics 2001, 20, 5139.
198. Scholtz, M. Ber. Dtsch. Chem. Ges. 1905, 38, 595.
199. Wedekind, E.; Ney, F. Ber. Dtsch. Chem. Ges. 1912, 45, 1298.
200. Wedekind, E.; Maiser, G. L. Ber. Dtsch. Chem. Ges. 1928, 61, 2471.
201. Shustov, G. V.; Zolotoi, A. B.; Zaichenko, N. L.; Dyachenko, O. A.; Atovmyan, L. O.; Kostayanovsky, R. G. Tetrahedron 1984, 40, 2151.
202. Bader, A.; Pabel, M.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1996, 35, 3874.
203. Vedejs, E.; Donde, Y. J. Am. Chem. Soc. 1997, 119, 9293.
204. Knowles, W. E. In Asymmetric Catalysis on Industrial Scale; Blaser, H. U., Schmidt, E., Eds.; Wiley-VCH: Weinbeim, Germany, 2004; pp 23-38.
205. Vedejs, E.; Donde, Y. J. Org. Chem. 2000, 65, 2337.
206. Vedejs, E.; Fields, S. C.; Schrimpf, M. R. J. Am. Chem. Soc. 1993, 115, 11612.
207. Vedejs, E.; Fields, S. C.; Lin, S.; Schrimpf, M. R. J. Org. Chem. 1995, 60, 3028.
208. Vedejs, E.; Fields, S. C.; Hayashi, R.; Hitchcock, S. R.; Powell, D. R.; Schrimpf, M. R. J. Am. Chem. Soc. 1999, 121, 2460.
209. Vedejs, E.; Chapman, R. W.; Lin, S,; Müller, M.; Powell, D. R. J. Am. Chem. Soc. 2000, 122, 3047.
210. Ebbers, E. J.; Ariaans, G. J. A.; Houbiers, J. P. M.; Bruggink, A.; Zwanenburg, B. Tetrahedron 1997, 53, 9417.