The diaryl(oxy)methyl group: More than an innocent bystander in chiral auxiliaries, catalysts, and dopants

Angewandte Chemie - International Edition

Volumn 51, Issue 11, 2012, Pages 2550-2562

  Braun, Manfred ^a  

^a HEINRICH HEINE UNIVERSITY   (Germany)

Author keywords

asymmetric synthesis; chirality; homogeneous catalysis; liquid crystals; synthetic methods

Indexed keywords

ARYL GROUP; ASYMMETRIC SYNTHESIS; BENEFICIAL EFFECTS; CHIRAL AUXILIARIES; CHIRAL DOPANT; CHIRAL MOLECULE; HOMOGENEOUS CATALYSIS; METHYL GROUP; ORGANOCATALYSTS; STRUCTURAL UNIT; SYNTHETIC METHODS;

CHIRALITY; FUNCTIONAL GROUPS; LIQUID CRYSTALS; METAL COMPLEXES; METHANOL; REACTION KINETICS; STEREOSELECTIVITY;

STEREOCHEMISTRY;

EID: 84858048951     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201105127     Document Type: Review

References (222)

1. M. Braun, Angew. Chem. 1996, 108, 565-568
2. Angew. Chem. Int. Ed. Engl. 1996, 35, 519-522; see also
3. D. Seebach, The Tagasako Times 2006, 157, 34-40.
4. R. M. Beesley, C. K. Ingold, J. F. Thorpe, J. Chem. Soc. Trans. 1915, 107, 1080-1106
5. E. L. Eliel, S. H. Wilen, Stereochemistry of Organic Compounds, Wiley, New York, 1994, pp. 682-684; for a recent discussion of the origin of the germinal dimethyl effect, see
6. A. L. Ringer, D. H. Magers, J. Org. Chem. 2007, 72, 2533-2537
7. S. M. Bachrach, J. Org. Chem. 2008, 73, 2466-2468.
8. For a favorable effect of the geminal diphenyl(oxy)methyl group on the formation of macrocyclic organoaluminum and organozinc systems, see, C. Redshaw, M. R. J. Elsegood, K. E. Holmes, Angew. Chem. 2005, 117, 1884-1887
9. Angew. Chem. Int. Ed. 2005, 44, 1850-1853
10. C. Redshaw, M. R. J. Elsegood, Angew. Chem. 2007, 119, 7597-7601
11. Angew. Chem. Int. Ed. 2007, 46, 7453-7457.
12. R. Noyori, Angew. Chem. 2002, 114, 2108-2123
13. Angew. Chem. Int. Ed. 2002, 41, 2008-2022.
14. S. Brunie, J. Mazan, N. Langlois, H. B. Kagan, J. Organomet. Chem. 1976, 114, 225-232.
15. D. Seebach, A. K. Beck, M. Schiess, L. Widler, A. Wonnacott, Pure Appl. Chem. 1983, 55, 1807-1822; TADDOL prototype 2 was first prepared by A. K. Beck and D. Seebach in 1982; see
16. D. Seebach, Chimia 2007, 61, 51-58.
17. D. Seebach, A. K. Beck, R. Imwinkelried, S. Roggo, A. Wonnacott, Helv. Chim. Acta 1987, 70, 954-974
18. A. K. Beck, B. Bastani, D. A. Plattner, W. Petter, D. Seebach, H. Braunschweiger, P. Gysi, L. La Vecchia, Chimia 1991, 45, 238-241
19. A. K. Beck, P. Gysi, L. La Vecchia, D. Seebach, Org. Synth. 1999, 76, 12-22.
20. For a comprehensive review on TADDOLs, see, D. Seebach, A. K. Beck, A. Heckel, Angew. Chem. 2001, 113, 96-142
21. Angew. Chem. Int. Ed. 2001, 40, 92-138
22. for more recent reviews on TADDOLs and their derivatives in asymmetric synthesis, see, H. Pellissier, Tetrahedron 2008, 64, 10279-10317
23. H. W. Lam, Synthesis 2011, 2011-2043.
24. R. O. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807-832, and references therein.
25. B. Schmidt, D. Seebach, Angew. Chem. 1991, 103, 100-101
26. Angew. Chem. Int. Ed. Engl. 1991, 30, 99-101
27. J. L. von dem Bussche-Hünnefeld, D. Seebach, Tetrahedron 1992, 48, 5719-5730
28. D. Seebach, A. K. Beck, B. Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363-4384.
29. D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang, D. Hunziker, W. Petter, Helv. Chim. Acta 1992, 75, 2171-2209
30. H. Schäfer, D. Seebach, Tetrahedron 1995, 51, 2305-2324.
31. Y. N. Yto, X. Ariza, A. K. Beck, A. Boháč, C. Ganter, R. E. Gawley, F. N. M. Kühnle, J. Tuleja, Y. M. Wamg, D. Seebach, Helv. Chim. Acta 1994, 77, 2071-2110.
32. See legend to Scheme 27 in Ref. [8a]. The fact that the hydrogenation product of TADDOL (cyclohexyl instead of phenyl) is another inefficient ligand has been attributed to steric rather than electronic reasons:, D. Seebach, R. Dahinden, R. E. Marti, A. K. Beck, D. A. Plattner, F. N. M. Kühnle, J. Org. Chem. 1995, 60, 1788-1799.
33. A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321-2336. It is worth mentioning that the low enantioselectivity obtained with the dimethyl derivative could be substantially increased when the Cp residue is replaced by the Cp* ligand.
34. M. Braun, R. Devant, Tetrahedron Lett. 1984, 25, 5031-5034.
35. M. Braun, S. Gräf, S. Herzog, Org. Synth. 1993, 72, 32-37
36. M. Braun, S. Gräf, Org. Synth. 1993, 72, 38-47
37. R. Devant, U. Mahler, M. Braun, Chem. Ber. 1988, 121, 397-406
38. M. Braun, D. Waldmüller, Synthesis 1989, 856-858; concerning the crucial role of the geminal diphenyl group in HYTRA, it should be mentioned that attempts to use the monoacetates of 1-phenyl-1,2-ethanediol in aldol reactions were less than satisfactory, including insufficient regiochemistry in the formation of the monoester, acyl migration, and marginal diastereoselectivity. This is in contrast to the results with N-acetylphenylglycinol, a reagent that provided an early solution to the acetate aldol problem, see
39. M. Braun, R. Devant, Angew. Chem. 1983, 95, 802-803
40. Angew. Chem. Int. Ed. Engl. 1983, 22, 788-789.
41. Angew. Chem. Int. Ed. Engl. 1987, 26, 24-37
42. M. Braun, in Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Weinheim, 2004, pp. 1-61; for more recent applications of the HYTRA aldol method in drug synthesis, see
43. J. E. Macor, G. Mullen, P, Verhoest, A. Sampognaro, B. Shepardson, R. A. Mack, J. Org. Chem. 2004, 69, 6493-6495
44. J.-P. Robin, J. Blanchard, L. Chauviat, R. Dhal, J.-P. Marie, N. Radosevic, US 20050090484, 2005
45. Y.-J. Kim, P. Wang, M. Navarro-Villalobos, B. D. Rhode, J. Derryberry, D. Y. Gin, J. Am. Chem. Soc. 2006, 128, 11906-11915
46. C. Faveau, M. Mondon, J.-P. Gesson, T. Mahnke, S. Gebhardt, U. Koert, Tetrahedron Lett. 2006, 47, 8305-8308
47. C. Lentsch, U. Rinner, Org. Lett. 2009, 11, 5326-5328
48. C. T. Brain, A. Chen, A. Nelson, N. Tanikkul, E. J. Thomas, Tetrahedron 2010, 66, 6613-6625.
49. B. D. Roth, C. J. Blankley, A. W. Chucholowski, E. Ferguson, M. L. Hoefle, D. F. Ortwine, R. S. Newton, C. S. Sekerke, D. R. Sliscovic, C. D. Stratton, M. Wilson, J. Med. Chem. 1991, 34, 357-366; for an improved HYTRA-based process for the preparation of atorvastatin, see
50. F. Wang, D. Che, B. R. Guntoori, Y. Zhao, A. C. Kinsman, J. Faught, A. Chow, WO 2006089401, 2006.
51. B. D. Roth, Prog. Med. Chem. 2002, 40, 1-22. Lipitor is considered the "bestselling pharmaceutical in history", see
52. J. Simons, CNN Money, January 20, 2003.
53. H. B. Kagan, F. Rebiere, Synlett 1990, 643-650; for more recent applications of this method, see
54. N. Díaz Buezo, J. C. de La Rosa, J. Priego, I. Alonso, J. C. Carretero, Chem. Eur. J. 2001, 7, 3890-3900
55. D. M. Freudendahl, M. Iwaoka, T. Wirth, Eur. J. Org. Chem. 2010, 3934-3944.
56. T. Hintermann, D. Seebach, Helv. Chim. Acta 1998, 81, 2093-2126.
57. J. C. D. Müller-Hartwieg, L. La Vecchia, H. Meyer, A. K. Beck, D. Seebach, Org. Synth. 2008, 85, 295-306.
58. S. D. Tilley, K. P. Reber, E. J. Sorensen, Org. Lett. 2009, 11, 701-703.
59. E. J. Corey, Pure Appl. Chem. 1990, 62, 1209-1216
60. V. K. Singh, Synthesis 1992, 605-617
61. E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092-2118
62. Angew. Chem. Int. Ed. 1998, 37, 1986-2012
63. B. T. Cho, Tetrahedron 2006, 62, 7621-7643; procedures for the preparation of (S)- and (R)-diphenylprolinol have been given in Organic Syntheses
64. L. C. Xavier, J. M. Mohan, D. J. Mathre, A. S. Thompson, J. D. Carroll, E. G. Corley, R. Desmond, Org. Synth. 1997, 74, 50
65. N. A. Nicolic, P. Beak, Org. Synth. 1997, 74, 23.
66. E. J. Corey, R. K. Bakshi, S. Shibata, J. Am. Chem. Soc. 1987, 109, 5551-5553
67. E. J. Corey, R. K. Bakshi, S. Shibata, C.-P. Chen, V. K. Singh, J. Am. Chem. Soc. 1987, 109, 7925-7926
68. E. J. Corey, S. Shibata, R. K. Bakshi, J. Org. Chem. 1988, 53, 2861-2863.
69. A. Hirao, S. Itsuno, S. Nakahama, N. Yamazaki, J. Chem. Soc. Chem. Commun. 1981, 315-317
70. S. Itsuno, M. Nakano, K. Miyazaki, H. Masuda, K. Ito, A. Hirao, S. Nakahama, J. Chem. Soc. Perkin Trans. 1 1985, 2039-2044.
71. S. Itsuno, M. Nakano, K. Ito, A. Hirao, M. Owa, N. Kanda, S. Nakahama, J. Chem. Soc. Perkin Trans. 1 1985, 2615-2619
72. C. Franot, G. B. Stone, P. Engeli, C. Spöndlin, E. Waldvogel, Tetrahedron: Asymmetry 1995, 6, 2755-2766
73. C. Caze, N. El Moualij, P. Hodge, C. J. Lock, J. Ma, J. Chem. Soc. Perkin Trans. 1 1995, 345-349
74. M. Felder, G. Giffels, C. Wandrey, Tetrahedron: Asymmetry 1997, 8, 1975-1977
75. G. Giffels, J. Beliczey, M. Felder, U. Kragl, Tetrahedron: Asymmetry 1998, 9, 691-696
76. C. Schunicht, A. Biffis, G. Wulff, Tetrahedron 2000, 56, 1693-1699
77. J.-B. Hu, G. Zhao, Z.-D. Ding, Angew. Chem. 2001, 113, 1143-1145
78. Angew. Chem. Int. Ed. 2001, 40, 1109-1111
79. M. D. Price, J. K. Sui, M. J. Kurth, N. E. Schore, J. Org. Chem. 2002, 67, 8086-8089
80. S. V. Luis, B. Altava, M. I. Burguete, M. Collado, J. Escorihuela, E. Garcia-Verdugo, M. J. Vincent, J. Martens, Ind. Eng. Chem. Res. 2003, 42, 5977-5982
81. S. Degni, C.-E. Wilén, A. Rosling, Tetrahedron: Asymmetry 2004, 15, 1495-1499
82. M. Braun, M. Sigloch, J. Cremer, Lett. Org. Chem. 2008, 5, 244-248.
83. A. S. Demir, E. Mecitoglu, C. Tanyeli, V. Gülbeyaz, Tetrahedron: Asymmetry 1996, 7, 3359-3364
84. E. J. Corey, J. O. Link, Tetrahedron Lett. 1989, 30, 6275-6278.
85. J. M. Brunel, M. Maffei, G. Buono, Tetrahedron: Asymmetry 1993, 4, 2255-2260.
86. T. Mehler, W. Behnen, J. Wilken, J. Martens, Tetrahedron: Asymmetry 1994, 5, 185-188.
87. J. Xu, T. Wei, S.-S. Lin, Q. Zhang, Helv. Chim. Acta 2005, 88, 180-186.
88. Itsuno et al. had already noticed that the efficiency of (S)-2-amino-3-methylbutanol (12, H instead of Ph) in borane reductions was enhanced significantly by introducing the gemial diphenyl group, see, S. Itsuno, A. Hirao, S. Nakahama, N. Yamazaki, J. Chem. Soc. Perkin Trans. 1 1983, 1673-1676. A similar beneficial effect was observed in RAMP- and SAMP-hydrazones, when the methoxymethyl side chain was replaced by diphenylmethoxymethyl; see
89. D. Enders, V. Bhushan, Tetrahedron Lett. 1988, 29, 2437-2440.
90. M. Braun, M. Sigloch, J. Cremer, Adv. Synth. Catal. 2007, 349, 337-342
91. W. Xu, H. Guo, J. Zhang, Q. Zhu, X. Hu, J. Mol. Catal. A 2009, 300, 25-28; for a recent experimental and theoretical study on the influence of the electronic properties of residues at the boron atom, see
92. T. Korenaga, K. Nomura, K. Onoue, T. Sakai, Chem. Commun. 2010, 46, 8624-8626.
93. D. K. Jones, D. C. Liotta, I. Shinkai, D. J. Mathre, J. Org. Chem. 1993, 58, 799-801
94. G. J. Quallich, J. F. Blake, T. M. Woodall, J. Am. Chem. Soc. 1994, 116, 8516-8525
95. V. Nevalainen, R. Uggla, M. R. Sundberg, Tetrahedron: Asymmetry 1995, 6, 1431-1440
96. C. Puigjaner, A. Vidal-Ferran, A. Moyano, A. M. Pericàs, A. Riera, J. Org. Chem. 1999, 64, 7902-7911
97. G. Bringmann, J. Hinrichs, J. Kraus, A. Wuzik, T. Schulz, J. Org. Chem. 2000, 65, 2517-2527.
98. G. Alagona, C. Ghio, M. Persico, S. Tomasi, J. Am. Chem. Soc. 2003, 125, 10027-10039.
99. For a recent review, see, E. J. Corey, Angew. Chem. 2009, 121, 2134-2151
100. Angew. Chem. Int. Ed. 2009, 48, 2100-2117.
101. E. J. Corey, T. Shibata, T. W. Lee, J. Am. Chem. Soc. 2002, 124, 3808-3809.
102. E. J. Corey, Angew. Chem. 2002, 114, 1724-1741
103. Angew. Chem. Int. Ed. 2002, 41, 1650-1667.
104. D. H. Ryu, T. W. Lee, E. J. Corey, J. Am. Chem. Soc. 2002, 124, 9992-9993
105. - as the counterion of the oxazaborolidine cation.
106. D. Liu, E. Canales, E. J. Corey, J. Am. Chem. Soc. 2007, 129, 1498-1499
107. J. N. Payette, H. Yamamoto, Angew. Chem. 2009, 121, 8204-8206
108. Angew. Chem. Int. Ed. 2009, 48, 8060-8062.
109. H. Brunner, C. Henrichs, Tetrahedron: Asymmetry 1995, 6, 653-656
110. H. Brunner, C. Blüchel, M. P. Doyle, J. Organomet. Chem. 1997, 541, 89-95
111. D. Seebach, E. Devaquet, A. Ernst, M. Hayakawa, F. N. M. Kühnle, W. B. Schweizer, B. Weber, Helv. Chim. Acta 1995, 78, 1636-1650
112. T. Robert, Z. Abiri, J. Wasssenaar, A. J. Sandee, S. Romanski, J.-M. Neudoerfl, H.-G. Schmalz, J. N. H. Reek, Organometallics 2010, 29, 478-483.
113. K. Soai, A. Ookawa, T. Kaba, K. Ogawa, J. Am. Chem. Soc. 1987, 109, 7111-7115
114. M. I. Burguete, E. Garcia-Verdugo, M. J. Vicent, S. V. Luis, H. Pennemann, N. Graf von Keyserling, J. Martens, Org. Lett. 2002, 4, 3947-3950
115. S. Superchi, E. Giorgio, P. Scafato, C. Rosini, Tetrahedron: Asymmetry 2002, 13, 1385-1391
116. M. Braun, R. Fleischer, B. Mai, M.-A. Schneider, S. Lachenicht, Adv. Synth. Catal. 2004, 346, 474-482
117. S. Rodríguez-Escrich, K. S. Reddy, C. Jimeno, G. Colet, C. Rodríguez-Escrich, L. Solà, A. Vidal-Ferran, M. A. Pericàs, J. Org. Chem. 2008, 73, 5340-5353.
118. H. Wally, M. Widhalm, W. Weissensteiner, K. Schlögl, Tetrahedron: Asymmetry 1993, 4, 285-288
119. M. Watanabe, S. Araki, Y. Butsugan, M. Uemura, J. Org. Chem. 1991, 56, 2218-2224
120. M. Watanabe, Synlett 1995, 1050-1052
121. P. I. Dosa, J. C. Ruble, G. C. Fu, J. Org. Chem. 1997, 62, 444-445
122. C. Bolm, K. Muñiz-Fernández, A. Seger, G. Raabe, K. Günther, J. Org. Chem. 1998, 63, 7860-7867
123. M. C. Wang, L.-T. Liu, J.-S. Zhang, Y.-Y. Shi, D.-K. Wang, Tetrahedron: Asymmetry 2004, 15, 3853-3859.
124. C. Bolm, J. Rudolph, J. Am. Chem. Soc. 2002, 124, 14850-14851.
125. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003-12004
126. B. M. Trost, E. L. Silcoff, H. Ito, Org. Lett. 2001, 3, 2497-2500
127. B. M. Trost, V. S. C. Yeh, Angew. Chem. 2002, 114, 889-891
128. Angew. Chem. Int. Ed. 2002, 41, 861-863
129. B. M. Trost, L. R. Terrell, J. Am. Chem. Soc. 2003, 125, 338-339
130. B. M. Trost, J. Jaratjaroonphong, V. Reutrakul, J. Am. Chem. Soc. 2006, 128, 2778-2779
131. B. M. Trost, C. Müller, J. Am. Chem. Soc. 2008, 130, 2438-2439
132. B. M. Trost, T. Mino, J. Am. Chem. Soc. 2003, 125, 2410-2411
133. B. M. Trost, A. H. Weiss, A. Jacobi von Wangelin, J. Am. Chem. Soc. 2006, 128, 8-9
134. B. M. Trost, V. S. Chan, D. Yamamoto, J. Am. Chem. Soc. 2010, 132, 5186-5192
135. D. Zhao, Y. Yuan, A. S. C. Chan, R. Wang, Chem. Eur. J. 2009, 15, 2738-2741
136. D. Zhao, Y. Wang, L. Mao, R. Wang, Chem. Eur. J. 2009, 15, 10983-10987
137. D. Zhao, L. Mao, D. Yang, R. Wang, J. Org. Chem. 2010, 75, 6756-6763
138. B. M. Trost, V. S. C. Yeh, H. Ito, N. Bremeyer, Org. Lett. 2002, 4, 2621-2623
139. N. Qi, R.-Z. Liao, J.-G. Yu, R.-Z. Liu, J. Comput. Chem. 2010, 31, 1376-1384.
140. It should be noted that in crystal-structure analyses of related bimetallic zinc complexes, an additional zinc-nitrogen coordination is observed:, C. J. Fahrni, A. Pfaltz, M. Neuburger, M. Zehnder, Helv. Chim. Acta 1998, 81, 507-524
141. S. Uhlenbrock, R. Wegner, B. Krebs, J. Chem. Soc. Dalton Trans. 1996, 3731-3736
142. H. Sakiyama, R. Mochizuki, A. Sugawara, M. Sakamoto, Y. Nishida, M. Yamasaki, J. Chem. Soc. Dalton Trans. 1999, 997-1000.
143. Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146
144. A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. USA 2004, 101, 5846-5850.
145. H. Du, D. Zhao, K. Ding, Chem. Eur. J. 2004, 10, 5964-5970
146. R. Villano, M. R. Acocella, A. Massa, L. Palombi, A. Scettri, Tetrahedron Lett. 2007, 48, 891-895.
147. J. D. McGilvra, A. K. Unni, K. Modi, V. H. Rawal, Angew. Chem. 2006, 118, 6276-6279
148. Angew. Chem. Int. Ed. 2006, 45, 6130-6133
149. V. B. Gondi, M. Gravel, V. H. Rawal, Org. Lett. 2005, 7, 5657-5660.
150. N. Momiyama, H. Yamamoto, J. Am. Chem. Soc. 2005, 127, 1080-1081.
151. D. J. Harriman, G. Deslongchamps, J. Mol. Model. 2006, 12, 793-797
152. D. J. Harriman, A. Lambropoulos, G. Deslongchamps, Tetrahedron Lett. 2007, 48, 689-692.
153. X. Zhang, H. Du, Z. Wang, Y.-D. Wu, K. Ding, J. Org. Chem. 2006, 71, 2862-2869.
154. C. D. Anderson, T. Dudding, R. Gordillo, K. N. Houk, Org. Lett. 2008, 10, 2749-2752.
155. For a few, selected reviews on organocatalysis, see, C. F. Barbas III, Angew. Chem. 2008, 120, 44-50
156. Angew. Chem. Int. Ed. 2008, 47, 42-47
157. A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716-4739
158. Angew. Chem. Int. Ed. 2008, 47, 4638-4660; special issue on organocatalysis
159. Chem. Rev. 2007, 107, 5413-5883
160. B. List, Chem. Commun. 2006, 819-824
161. "Asymmetric Organocatalysis": (Ed.: B. List), Top. Curr. Chem. 2010, 291.
162. D. Seebach, U. Grošelj, D. M. Badine, W. B. Schweizer, A. K. Beck, Helv. Chim. Acta 2008, 91, 1999-2034.
163. M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804-807
164. Angew. Chem. Int. Ed. 2005, 44, 794-797.
165. Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284-4287
166. Angew. Chem. Int. Ed. 2005, 44, 4212-4215.
167. To the best of our knowledge, the diphenylsilyloxymethyl motif was used for the first time in asymmetric synthesis in the form of a triphenylglycol- derived propionate:, M. Braun, H. Sacha, Angew. Chem. 1991, 103, 1369-1371
168. Angew. Chem. Int. Ed. Engl. 1991, 30, 1318-1320; the crucial role of silyl protection in diarylprolinols as organocatalysts has been demonstrated recently by NMR spectroscopy of the diphenylprolinol-derived enamines, which reveals that, without protection of the oxygen atom, oxazolidine formation occurs, which leads to a dead end of the organocatalysis
169. M. B. Schmid, K. Zeitler, R. M. Gschwind, J. Am. Chem. Soc. 2011, 133, 7065-7074.
170. For a recent review, see, S. Bertelsen, K. A. Jørgensen, Chem. Soc. Rev. 2009, 38, 2178-2189.
171. P. Dinér, M. Nielsen, M. Marigo, K. A. Jørgensen, Angew. Chem. 2007, 119, 2029-2033
172. Angew. Chem. Int. Ed. 2007, 46, 1983-1987.
173. For short reviews, see, D. Enders, G. Grondal, M. R. M. Hüttl, Angew. Chem. 2007, 119, 1590-1601
174. Angew. Chem. Int. Ed. 2007, 46, 1570-1581
175. B. Westermann, M. Ayaz, S. S. van Berkel, Angew. Chem. 2010, 122, 858-861
176. Angew. Chem. Int. Ed. 2010, 49, 846-849. New amino alcohols featuring a diphenylhydroxy or diphenyl(silyloxy)moiety with application in orgnocatalysis are continually reported, see for example
177. M. Raj, Vishnumaya, S. K. Ginotra, V. K. Singh, Org. Lett. 2006, 8, 4097-4099
178. J. Pietruszka, R. C. Simon, Chem. Eur. J. 2010, 16, 14534-14544
179. O. V. Maltsev, A. S. Kucherenko, A. L. Chimishkyan, S. G. Zlotin, Tetrahedron: Asymmetry 2010, 21, 2659-2670
180. B. Wang, X.-W. Liu, L.-Y. Liu, W.-X. Chang, J. Li, Eur. J. Org. Chem. 2010, 5951-5954
181. R. S. Rambo, P. H. Schneider, Tetrahedron: Asymmetry 2010, 21, 2254-2257
182. T. Kano, H. Mii, K. Maruoka, Angew. Chem. 2010, 122, 6788-6791
183. Angew. Chem. Int. Ed. 2010, 49, 6638-6641
184. O. V. Maltsev, A. S. Kucherenko, I. P. Beletskaya, V. A. Tartakovsky, S. G. Zlotin, Eur. J. Org. Chem. 2010, 2927-2933
185. P.-L. Shao, X.-Y. Chen, L.-H. Sun, S. Ye, Tetrahedron Lett. 2010, 51, 2316-2318
186. Z.-Y. Xue, Y. Jiang, W.-C. Yuan, X.-M. Zhang, Eur. J. Org. Chem. 2010, 616-619
187. H. Zhang, S. Zhang, L. Liu, G. Luo, W. Duan, W. Wang, J. Org. Chem. 2010, 75, 368-374
188. M. Lombardo, M. Chiarucci, A. Quintavalla, C. Trombini, Adv. Synth. Catal. 2009, 351, 2801-2806
189. L. Baragwanath, C. A. Rose, K. Zeitler, S. J. Connon, J. Org. Chem. 2009, 74, 9214-9217
190. X. Ma, C.-S. Da, L. Yi, Y.-N. Jia, Q.-P. Guo, L.-P. Che, F.-C. Wu, J.-R. Wang, W.-P. Li, Tetrahedron: Asymmetry 2009, 20, 1419-1424
191. S.-W. Wang, J. Chen, G.-H. Chen, Y.-G. Peng, Synlett 2009, 1457-1462
192. Y. Okuyama, H. Nakano, Y. Watanabe, M. Makabe, M. Takeshita, K. Uwai, C. Kabuto, E. Kwon, Tetrahedron Lett. 2009, 50, 193-197.
193. C. J. Booth, in Handbook of Liquid Crystals, Vol. 2A (Eds.:, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, V. Vill,), Wiley-VCH, Weinheim, 1998, chap. IV, pp. 303-334
194. H. Coles, in Handbook of Liquid Crystals, Vol. 2A (Eds.:, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, V. Vill,), Wiley-VCH, Weinheim, 1998, chap. IV, pp. 335-410
195. S. M. Kelly, in Handbook of Liquid Crystals, Vol. 2B (Eds.:, D. Demus, J. Goodby, G. W. Gray, H.-W. Spiess, V. Vill,), Wiley-VCH, Weinheim, 1998, chap. VI, pp. 493-514
196. F. Vögtle, Supramolekulare Chemie, Teubner, Stuttgart, 1992.
197. G. Solladié, R. G. Zimmermann, Angew. Chem. 1984, 96, 335-349
198. Angew. Chem. Int. Ed. Engl. 1984, 23, 348-362
199. Chirality in Liquid Crystals (Series on Partially Ordered Systems) (Eds.: C. Bahr, H.-S. Kitzerow), Springer, Heidelberg, 2001
200. R. Eelkema, B. L. Feringa, Org. Biomol. Chem. 2006, 4, 3729-3745
201. S. Pieraccini, A. Ferrarini, G. P. Spada, Chirality 2008, 20, 749-759
202. S. Pieraccini, S. Masiero, A. Ferrarini, G. P. Spada, Chem. Soc. Rev. 2011, 40, 258-271.
203. G. Heppke, D. Lötzsch, F. Oestreicher, Z. Naturforsch. 1986, 41, 1214-1218. Nevertheless, dopants with lower HTP values seem to be sufficient for industrial application, see
204. M. Paul, Dissertation, Universität Hamburg, 2000.
205. H.-G. Kuball, B. Weiß, A. K. Beck, D. Seebach, Helv. Chim. Acta 1997, 80, 2507-2514.
206. A. F. Drake, G. Gottarelli, G. P. Spada, Chem. Phys. Lett. 1984, 110, 630-633
207. Y. Matsuoka, H. Sato, A. Yamagishi, K. Okamoto, N. Hoshino, Chem. Mater. 2005, 17, 4910-4917
208. G. Piao, K. Akagi, H. Shirakawa, Synth. Met. 1999, 101, 92-93
209. K. Hamakubo, S. Hama, S. Yagi, H. Nakazumi, T. Mizutani, Chem. Lett. 2005, 34, 1454-1455
210. H. Sato, A. Yamagishi, Int. J. Mol. Sci. 2009, 10, 4559-4574.
211. The descriptors C ("clockwise") and A (" anticlockwise") are used to indicate the configuration at the stereogenic metal atom. For a definition of these descriptors, see, M. F. Brown, B. R. Cook, T. E. Sloan, Inorg. Chem. 1975, 14, 1273-1278
212. G. J. Leigh, Nomenclature of Inorganic Chemistry: Recommendations, Vol. 1, Blackwell, Oxford, 1990
213. A. von Zelewsky, Stereochemistry of Coordination Compounds, Vol. 1, Wiley, New York, 1996.
214. M. Braun, A. Hahn, M. Engelmann, R. Fleischer, W. Frank, C. Kryschi, S. Haremza, K. Kürschner, R. Parker, Chem. Eur. J. 2005, 11, 3405-3412
215. M. Engelmann, M. Braun, H.-G. Kuball, Liq. Cryst. 2007, 34, 73-77
216. S. Schlecht, W. Frank, M. Braun, Eur. J. Org. Chem. 2010, 3721-3731.
217. Various attempts have been made to study the interaction between the dopant and nematic phase, most of them being based upon physical methods and theoretical calculations:, W. J. A. Gossens, Mol. Cryst. Liq. Cryst. 1971, 12, 237-244
218. G. Gottarelli, G. P. Spada, Mol. Cryst. Liq. Cryst. 1985, 123, 377-388
219. Y. K. Yarovoy, M. M. Labes, Mol. Cryst. Liq. Cryst. 1995, 270, 101-112
220. H.-G. Kuball, H. Brüning, Chirality 1997, 9, 407-423
221. G. Celebre, G. De Luca, M. Maiorino, F. Iemma, A. Ferrarini, S. Pieraccini, G. P. Spada, J. Am. Chem. Soc. 2005, 127, 11736-11744. See also ref. [64b,d, 67b,e].
222. The state of the art was reflected by the classic "Asymmetric Organic Reactions" by Morrison and Mosher that was considered comprehensive at that time:, J. D. Morrison, H. S. Mosher, Asymmetric Organic Reactions, American Chemical Society, Washington, DC, 1976.