Chiral phosphoric acids as versatile catalysts for enantioselective carbon-carbon bond forming reactions

Bulletin of the Chemical Society of Japan

Volumn 83, Issue 2, 2010, Pages 101-119

  Terada, Masahiro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2-NAPHTHOLS; ACID CATALYST; BRONSTED ACIDS; CARBON-CARBON BOND; CHEMICAL FEATURES; CHIRAL ENVIRONMENT; CONFORMATIONAL FLEXIBILITY; DOUBLE BONDS; DUAL FUNCTION; ELECTRON-RICH; ELECTRONIC INFLUENCE; ENANTIOSELECTIVE; ENANTIOSELECTIVE CATALYSTS; ENANTIOSELECTIVE REACTIONS; ENANTIOSELECTIVE TRANSFORMATION; MONOFUNCTIONAL; PHOSPHORYL OXYGEN; RING SYSTEMS; STRONG ACIDS; SUBSTRATE RECOGNITION SITES;

ALDEHYDES; CATALYSTS; CHEMICAL BONDS; ETHERS; OXYGEN; PHENOLS; PHOSPHORIC ACID;

CATALYSIS;

EID: 77149142297     PISSN: 00092673     EISSN: 13480634     Source Type: Journal    
DOI: 10.1246/bcsj.20090268     Document Type: Article

References (194)

1. For recent reviews, see: a) A. Berkessel, H. Gröger, Asymmetric Organocatalysis-From Biomimetic Concepts to Powerful Methods for Asymmetric Synthesis,Wiley-VCH, Weinheim, 2005.
2. b)M.S.Taylor, E. N. Jacobsen, Angew. Chem., Int. Ed. 2006, 45, 1520.
3. c) Enantioselective Organocatalysis: Reactions and Experimental Procedures, ed. by P. I. Dalko, Wiley-VCH, New York, 2007.
4. For recent reviews, see: a) T. Akiyama, J. Itoh, K. Fuchibe, Adv. Synth. Catal. 2006, 348, 999.
5. b) A. G. Doyle, E. N. Jacobsen, Chem. Rev. 2007, 107, 5713.
6. c) T. Akiyama, Chem. Rev. 2007, 107, 5744.
7. d) X. Yu, W. Wang, Chem. Asian J. 2008, 3, 516.
8. a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901.
9. b) M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem., Int. Ed. 2000, 39, 1279.
10. c) P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012.
11. a) Y. Huang, A. K. Unni, A. N. Thadani, V. H. Rawal, Nature 2003, 424, 146.
12. b) Also see: N. T. McDougal, S. E. Schaus, J. Am. Chem. Soc. 2003, 125, 12094.
13. c) B. M. Nugent, R. A. Yoder, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 3418.
14. Thiourea and urea: a) F. G. Bordwell,D.J.Algrim, J. A. Harrelson, Jr., J. Am. Chem. Soc. 1988, 110, 5903.
15. Aliphatic alcohols: b) F. G. Bordwell, R. J. McCallum, W. N. Olmstead, J. Org. Chem. 1984, 49, 1424.
16. c) W. N. Olmstead, Z. Margolin, F. G. Bordwell, J. Org. Chem. 1980, 45, 3295.
17. M. Terada, Chem. Commun. 2008, 4097.
18. S. J. Connon, Angew. Chem., Int. Ed. 2006, 45, 3909.
19. G.A.Olah, P. G. K. Surya, J. Sommer, Superacids, John
20. Wiley & Sons, New York, 1985.
21. L. D. Quin, A Guide to Organophosphorus Chemistry, John Wiley & Sons, New York, 2000, pp. 133-168.
22. For a review on asymmetric bifunctional catalysts, see: M. Shibasaki, M. Kanai, K. Funabashi, Chem. Commun. 2002, 1989.
23. For reviews, see: a) L. Pu, Chem. Rev. 1998, 98, 2405.
24. b) P. Kočovský, Š. Vyskočil, M. Smrčina, Chem. Rev. 2003, 103, 3213.
25. c) J. M. Brunel, Chem. Rev. 2005, 105, 857.
26. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem., Int. Ed. 2004, 43, 1566.
27. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356.
28. For binaphthol derived monophosphoricacids as a chiral ligand for transition or rare earth metal catalysts, see: a) H. Alper, N. Hamel, J. Am. Chem. Soc. 1990, 112, 2803.
29. b) N. McCarthy, M. A. McKervey, T. Ye, M. McCann, E. Murphy, M. P. Doyle, Tetrahedron Lett. 1992, 33, 5983.
30. c) M. C. Pirrung, J. Zhang, Tetrahedron Lett. 1992, 33, 5987.
31. d) J. Inanaga, Y. Sugimoto, T. Hanamoto, New J. Chem. 1995, 19, 707.
32. e) H. Furuno, T. Hanamoto, Y. Sugimoto, J. Inanaga, Org. Lett. 2000, 2, 49.
33. f) X. L. Jin, H. Sugihara, K. Daikai, H. Tateishi,Y.Z.Jin, H. Furuno, J. Inanaga, Tetrahedron 2002, 58, 8321.
34. g) H. Furuno, T. Hayano, T. Kambara, Y. Sugimoto, T. Hanamoto, Y. Tanaka, Y. Z. Jin, T. Kagawa, J. Inanaga, Tetrahedron 2003, 59, 10509.
35. h) C. A. Merlic, A. L. Zechman, Synthesis 2003, 1137.
36. For a review, see: M. Terada, N. Momiyama, in Chiral Amine Synthesis. Methods, Developments and Applications, ed. by T. Nugent, Wiley-VCH, Weinheim, in press.
37. For general reviews, see: a) M. Arend, B. Westermann, N. Risch, Angew. Chem., Int. Ed. 1998, 37, 1044.
38. b) S. K. Bur, S. F. Martin, Tetrahedron 2001, 57, 3221.
39. c) A. Córdova, Acc. Chem. Res. 2004, 37, 102.
40. For recent reviews, see: a) A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797.
41. b) J. M. M. Verkade, L. J. C. van Hemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29.
42. I. D. Gridnev, M. Kouchi, K. Sorimachi, M. Terada, Tetrahedron Lett. 2007, 48, 497.
43. T. Akiyama, Y. Saitoh, H. Morita, K. Fuchibe, Adv. Synth. Catal. 2005, 347, 1523.
44. M. Terada, K. Sorimachi, D. Uraguchi, Synlett 2006, 133.
45. For reviews, see: a) K. A. Jørgensen, Synthesis 2003, 1117.
46. b) M. Bandini,A.Melloni, A. Umani-Ronchi, Angew. Chem., Int. Ed. 2004, 43, 550.
47. c) T. B. Poulsen, K. A. Jørgensen, Chem. Rev. 2008, 108, 2903.
48. d) S.-L. You, Q. Cai, M. Zeng, Chem. Soc. Rev. 2009, 38, 2190.
49. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2004, 126, 11804.
50. Q. Kang, Z.-A. Zhao, S.-L. You, J. Am. Chem. Soc. 2007, 129, 1484.
51. G. B. Rowland, E. B. Rowland, Y. Liang, J. A. Perman, J. C. Antilla, Org. Lett. 2007, 9, 2609.
52. M. Terada, S. Yokoyama, K. Sorimachi, D. Uraguchi, Adv. Synth. Catal. 2007, 349, 1863.
53. Q. Kang, Z.-A. Zhao, S.-L. You, Tetrahedron 2009, 65, 1603.
54. M. J. Wanner, P. Hauwert, H. E. Schoemaker, R. de Gelder, J. H. van Maarseveen, H. Hiemstra, Eur. J. Org. Chem. 2008, 180.
55. G. Li, G. B. Rowland, E. B. Rowland, J. C. Antilla, Org. Lett. 2007, 9, 4065.
56. S. Nakamura, Y. Sakurai, H. Nakashima, N. Shibata, T. Toru, Synlett 2009, 1639.
57. Q. Kang, X.-J. Zheng, S.-L. You, Chem. - Eur. J. 2008, 14, 3539.
58. a) M. A. Ciufolini, C. Y. Wood, Tetrahedron Lett. 1986, 27, 5085.
59. b) M. A. Ciufolini, C. Y. W. Hermann, Q. Dong, T. Shimizu, S. Swaminathan, N. Xi, Synlett 1998, 105.
60. c) M. H. Haukaas, G. A. O'Doherty, Org. Lett. 2001, 3, 401.
61. d) J. M. Harris, A. Padwa, J. Org. Chem. 2003, 68, 4371.
62. For reviews, see: a) A. Aygun, U. Pindur, Curr. Med. Chem. 2003, 10, 1113.
63. b) G. W. Gribble, Pure Appl. Chem. 2003, 75, 1417.
64. c) H. Sings, S. Singh, Alkaloids 2003, 60, 51.
65. d) M. Somei, F. Yamada, Nat. Prod. Rep. 2004, 21, 278.
66. e) M. Somei,F. Yamada, Nat. Prod. Rep. 2005, 22, 73.
67. a) J. C. Antilla, W. D. Wulff, Angew. Chem., Int. Ed. 2000, 39, 4518.
68. b) M. Redlich, M. M. Hossain, Tetrahedron Lett. 2004, 45, 8987, and references cited therein.
69. A. L. Williams, J. N. Johnston, J. Am. Chem. Soc. 2004, 126, 1612, and references cited therein.
70. D. Uraguchi, K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2005, 127, 9360.
71. T. Hashimoto, K. Maruoka, J. Am. Chem. Soc. 2007, 129, 10054.
72. a) T. Akiyama, T. Suzuki, K. Mori, Org. Lett. 2009, 11, 2445.
73. Also see: b) X. Zeng, X. Zeng, Z. Xu, M. Lu, G. Zhong, Org. Lett. 2009, 11, 3036.
74. c) T. Hashimoto, N. Uchiyama, K. Maruoka, J. Am. Chem. Soc. 2008, 130, 14380.
75. Imines: a) R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem., Int. Ed. 2004, 43, 1679.
76. b) H. Kiyohara, R. Matsubara, S. Kobayashi, Org. Lett. 2006, 8, 5333.
77. Glyoxylate: c) R. Matsubara, Y. Nakamura, S. Kobayashi, Angew. Chem., Int. Ed. 2004, 43, 3258.
78. d) R. Matsubara, P. Vital, Y. Nakamura, H. Kiyohara, S. Kobayashi, Tetrahedron 2004, 60, 9769.
79. e) R. Matsubara, N. Kawai, S. Kobayashi, Angew. Chem., Int. Ed. 2006, 45, 3814.
80. f) R. Matsubara, T. Doko, R. Uetake, S. Kobayashi, Angew. Chem., Int. Ed. 2007, 46, 3047.
81. For some excellent studies of low loading of organocatalyst (less than 0.5 mol%), see: a) J. T. Su, P. Vachal, E. N. Jacobsen, Adv. Synth. Catal. 2001, 343, 197.
82. b) S. Saaby, M. Bella, K. A. Jørgensen, J.Am. Chem. Soc. 2004, 126, 8120.
83. c) S. Shirakawa, K. Yamamoto, M. Kitamura, T. Ooi, K. Maruoka, Angew. Chem., Int. Ed. 2005, 44, 625.
84. d) M. Kitamura, S. Shirakawa, K. Maruoka, Angew. Chem., Int. Ed. 2005, 44, 1549.
85. e) M. Terada, H. Ube, Y. Yaguchi, J. Am. Chem. Soc. 2006, 128, 1454.
86. f) M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044.
87. g) C. H. Cheon, H. Yamamoto, J. Am. Chem. Soc. 2008, 130, 9246.
88. h) X. Liu, B. Sun, L. Deng, Synlett 2009, 1685.
89. M. Terada, K. Machioka, K. Sorimachi, Angew. Chem., Int. Ed. 2006, 45, 2254.
90. For a recent review, see: D. Enders, C. Grondal,M.R.M. Httl, Angew. Chem., Int. Ed. 2007, 46, 1570.
91. M. Terada, K. Machioka, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 10336.
92. In situ generation of N-acylimines from α-amido sulfones under phase-transfer conditions. For a review, see: a) M. Petrini, Chem. Rev 2005, 105, 3949.
93. For selected recent examples of Mannich reactions, see: b) F. Fini, L. Bernardi, R. P. Herrera, D. Pettersen, A. Ricci, V. Sgarzani, Adv. Synth. Catal. 2006, 348, 2043.
94. c) T. Ollevier, E. Nadeau, J.-C. Eguillon, Adv. Synth. Catal. 2006, 348, 2080.
95. d) J. Song, H.-W. Shih, L. Deng, Org. Lett. 2007, 9, 603.
96. e) B. Niess, K. A. Jørgensen, Chem. Commun. 2007, 1620.
97. f) S. Lou, P. Dai, S. E. Schaus, J. Org. Chem. 2007, 72, 9998.
98. g) O. Marianacci,G. Micheletti, L. Bernardi,F.Fini, M. Fochi,D. Pettersen, V. Sgarzani,A.Ricci, Chem. - Eur. J. 2007, 13, 8338.
99. h) X. Xu, K. Wang, S. G. Nelson, J. Am. Chem. Soc. 2007, 129, 11690.
100. i) C.Gianelli, L. Sambri, A. Carlone, G. Bartoli,P. Melchiorre, Angew. Chem., Int. Ed. 2008, 47, 8700.
101. a) C. Gaulon, P. Gizecki, R. Dhal, G. Dujardin, Synlett 2002, 952.
102. b) M. Prashad, Y. Lu, O. Repič, J. Org. Chem. 2004, 69, 584.
103. M. Terada, K. Machioka, K. Sorimachi, Angew. Chem., Int. Ed. 2009, 48, 2553.
104. a) J. W. Yang, M. Stadler, B. List, Angew. Chem., Int. Ed. 2007, 46, 609.
105. b) H. Zhang, S. Mitsumori, N. Utsumi, M. Imai,N. Garcia-Delgado, M. Mifsud, K. Albertshofer, P. H.-Y. Cheong, K. N. Houk, F. Tanaka, C. F. Barbas, III, J.Am. Chem. Soc. 2008, 130, 875.
106. c) T. Kano, Y. Yamaguchi, K. Maruoka, Angew. Chem., Int. Ed. 2009, 48, 1838, and references cited therein.
107. M. Terada, Y. Toda, J. Am. Chem. Soc. 2009, 131, 6354.
108. a) H. Frauenrath, T. Arenz, G. Raabe, M. Zorn, Angew. Chem., Int. Ed. Engl. 1993, 32, 83.
109. b) T. Arenz, H. Frauenrath, G. Raabe, M. Zorn, Liebigs Ann. Chem. 1994, 931.
110. c) E. Tayama, S. Otoyama, W. Isaka, Chem. Commun. 2008, 4216.
111. a) A. N. Thadani, A. R. Stankovic, V. H. Rawal, Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5846.
112. b) H. Du, D. Zhao, K. Ding, Chem. - Eur. J. 2004, 10, 5964.
113. c) A. K. Unni, N. Takenaka, H. Yamamoto, V. H. Rawal, J. Am. Chem. Soc. 2005, 127, 1336.
114. d) V. B. Gondi, M. Gravel, V. H. Rawal, Org. Lett. 2005, 7, 5657.
115. e) W. Zhuang, T. B. Poulsen, K. A. Jørgensen, Org. Biomol. Chem. 2005, 3, 3284.
116. f) T. Tonoi,K.Mikami, Tetrahedron Lett. 2005, 46, 6355.
117. g) J. D. McGilvra, A. K. Unni, K. Modi, V. H. Rawal, Angew. Chem., Int. Ed. 2006, 45, 6130.
118. Intramolecular reaction, see: h) L. Zu, J. Wang, H. Li,H.Xie, W. Jiang, W. Wang, J. Am. Chem. Soc. 2007, 129, 1036.
119. Also see: i) P. R. Schreiner, Chem. Soc. Rev. 2003, 32, 289.
120. j) T. Schuster, M. Bauch, G. Dürner, M. W. Göbel, Org. Lett. 2000, 2, 179.
121. Activation of ketones by chiral phosphoricacids, see: a) T. Akiyama, T. Katoh, K. Mori, Angew. Chem., Int. Ed. 2009, 48, 4226.
122. b) J. Nie, G.-W. Zhang, L. Wang, A. Fu, Y. Zheng, J.-A. Ma, Chem. Commun. 2009, 2356.
123. Activation of ketones by N-triflyl phosphoramides, see: c) D. Nakashima, H. Yamamoto, J. Am. Chem. Soc. 2006, 128, 9626.
124. d) M. Rueping, W. Ieawsuwan, A. P. Antonchick, B. J. Nachtsheim, Angew. Chem., Int. Ed. 2007, 46, 2097.
125. e) M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem., Int. Ed. 2008, 47, 593.
126. f) M. Zeng, Q. Kang, Q.-L. He, S.-L. You, Adv. Synth. Catal. 2008, 350, 2169.
127. g) M. Rueping, T. Theissmann, A. Kuenkel, R. M. Koenigs, Angew. Chem., Int. Ed. 2008, 47, 6798.
128. Activation of other functionalities by chiral phosphoric acids or their derivatives: Aziridines: a) E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 12084.
129. b) G. D. Sala, A. Lattanzi, Org. Lett. 2009, 11, 3330.
130. Nitrones: c) P. Jiao, D. Nakashima, H. Yamamoto, Angew. Chem., Int. Ed. 2008, 47, 2411.
131. Nitroalkenes: d) J. Itoh, K. Fuchibe, T. Akiyama, Angew. Chem., Int. Ed. 2008, 47, 4016.
132. e) Y.-F. Sheng, G.-Q. Li, Q. Kang, A.-J. Zhang, S.-L. You, Chem. - Eur. J. 2009, 15, 3351.
133. f) Y.-F. Sheng, Q. Gu, A.-J. Zhang, S.-L. You, J. Org. Chem. 2009, 74, 6899.
134. Azomethine ylide: g) X.-H. Chen, W.-Q. Zhang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 5652.
135. h) W.-J. Liu, X.-H. Chen, L.-Z. Gong, Org. Lett. 2008, 10, 5357.
136. i) X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 13819.
137. Alcohols: j) F.-L. Sun, M. Zeng, Q. Gu, S.-L. You, Chem. - Eur. J. 2009, 15, 8709.
138. k) Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, L.-Z. Gong, Org. Lett. 2009, 11, 4620.
139. M. Terada, K. Soga, N. Momiyama, Angew. Chem., Int. Ed. 2008, 47, 4122.
140. M. Terada, T. Ikehara, H. Ube, J. Am. Chem. Soc. 2007, 129, 14112, and references cited therein.
141. For X-ray analysisof double hydrogen-bonding interaction between carboxylicacid and dimethylformamide, see: a) M. Czugler, J. J. Stezowski, E. Weber, J. Chem. Soc., Chem. Commun. 1983, 154.
142. b) I. Csöregh, A. Sjögren, M. Czugler, M. Cserzö, E. Weber, J. Chem. Soc., Perkin Trans. 2 1986, 507.
143. For hydrogen bonding in complexes of Lewisacids with formyl C-H hydrogen, see: E. J. Corey, T. W. Lee, Chem. Commun. 2001, 1321.
144. a) T. Ooi, K. Maruoka, in Comprehensive Asymmetric Catalysis, eds. by E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Springer-Verlag, Berlin, 1999,Vol. 3, pp. 1237-1254.
145. b) K. A. Jørgensen, in Cycloaddition Reactions in Organic Synthesis, ed. by S. Kobayashi, K. A. Jørgensen, Wiley-VCH, Weinheim, 2002, pp. 151-186.
146. For representative recent reviews of asymmetric hetero Diels-Alder reactions, see: a) K. A. Jørgensen, Angew. Chem., Int. Ed. 2000, 39, 3558.
147. b) K. A. Jorgensen, Eur. J. Org. Chem. 2004, 2093.
148. c) L. Lin, X. Liu, X. Feng, Synlett 2007, 2147.
149. For representative examples of catalytic enantioselective hetero Diels-Alder reactions of aldehydes with siloxy- or methoxydienes, see: a) K. Mikami, Y. Motoyama, M. Terada, J. Am. Chem. Soc. 1994, 116, 2812.
150. b) A. G. Dossetter, T. F. Jamison, E. N. Jacobsen, Angew. Chem., Int. Ed. 1999, 38, 2398.
151. c) M. Quitschalle, M. Christmann, U. Bhatt, M. Kalesse, Tetrahedron Lett. 2001, 42, 1263.
152. a) S. J. Danishefsky, E. Larson, D. Askin, N. Kato, J. Am. Chem. Soc. 1985, 107, 1246.
153. b) J. Jurczak, A. Golebiowski,A. Rahm, Tetrahedron Lett. 1986, 27, 853.
154. c) M. A. McCarrick, Y. D. Wu, K. N. Houk, J. Org. Chem. 1993, 58, 3330.
155. d) X. Zhang, H. Du, Z. Wang, Y.-D. Wu, K. Ding, J. Org. Chem. 2006, 71, 2862.
156. Only one exampleof the catalytic asymmetric anti-selective hetero Diels-Alder reaction has been reported using Danishefsky'sdienes. See: Y. Yamashita, S. Saito, H. Ishitani,S. Kobayashi, J. Am. Chem. Soc. 2003, 125, 3793.
157. N. Momiyama, H. Tabuse, M. Terada, J. Am. Chem. Soc. 2009, 131, 12882.
158. The double hydrogen-bonding model of the TS structure has been proposed on the basisof our previous report, see Ref. 52. 63 M. Terada, K. Sorimachi, J. Am. Chem. Soc. 2007, 129, 292.
159. Y.-X. Jia, J. Zhong, S.-F. Zhu, C.-M. Zhang, Q.-L. Zhou, Angew. Chem., Int. Ed. 2007, 46, 5565.
160. M. Terada, H. Tanaka, K. Sorimachi, Synlett 2008, 1661.
161. a) S. Mayer, B. List, Angew. Chem., Int. Ed. 2006, 45, 4193, and references cited therein.
162. Also see: b) X. Wang, B. List, Angew. Chem., Int. Ed. 2008, 47, 1119.
163. c) G. L. Hamilton, T. Kanai, F. D. Toste, J. Am. Chem. Soc. 2008, 130, 14984.
164. S. E. Reisman, A. G. Doyle, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 7198.
165. For a review on syntheticutility of azlactones, see: J. S. Fisk, R. A. Mosey, J. J. Tepe, Chem. Soc. Rev. 2007, 36, 1432.
166. M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430.
167. a) M. Rueping, A. P. Antonchick, C. Brinkmann, Angew. Chem., Int. Ed. 2007, 46, 6903.
168. b) W. Hu, X. Xu, J. Zhou, W.-J. Liu, H. Huang, J. Hu, L. Yang, L.-Z. Gong, J. Am. Chem. Soc. 2008, 130, 7782.
169. K. Sorimachi, M. Terada, J. Am. Chem. Soc. 2008, 130, 14452.
170. Z.-Y. Han, H. Xiao, X.-H. Chen, L.-Z. Gong, J. Am. Chem. Soc. 2009, 131, 9182.
171. For selected examples of enantioselective transfer hydrogenation reactions catalyzed by chiral phosphoricacids, see: a) M. Rueping, E. Sugiono, C. Azap, T. Theissmann, M. Bolte, Org. Lett. 2005, 7, 3781.
172. b) S. Hoffmann, A. M. Seayad, B. List, Angew. Chem., Int. Ed. 2005, 44, 7424.
173. c) R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84.
174. d) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem., Int. Ed. 2006, 45, 3683.
175. e) M. Rueping, A. P. Antonchick, T. Theissmann, Angew. Chem., Int. Ed. 2006, 45, 6751.
176. f) S. Hoffmann, M. Nicoletti,B.List, J. Am. Chem. Soc. 2006, 128, 13074.
177. g) G. Li,Y. Liang, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 5830.
178. h) M. Rueping, A. P. Antonchick, Angew. Chem., Int. Ed. 2007, 46, 4562.
179. i) Q. Kang, Z.-A. Zhao, S.-L. You, Adv. Synth. Catal. 2007, 349, 1657.
180. j) Q.-S. Guo, D.-M. Du, J. Xu, Angew. Chem., Int. Ed. 2008, 47, 759.
181. k) C. Zhu, T. Akiyama, Org. Lett. 2009, 11, 4180.
182. For selected recent examples, see: C-P bond formation: a) T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 2583.
183. b) X. Cheng, R. Goddard, G. Buth, B. List, Angew. Chem., Int. Ed. 2008, 47, 5079.
184. C-N bond formation: c) G. B. Rowland, H. Zhang, E. B. Rowland, S. Chennamadhavuni, Y. Wang, J. C. Antilla, J. Am. Chem. Soc. 2005, 127, 15696.
185. d) X. Cheng, S. Vellalath, R. Goddard, B. List, J. Am. Chem. Soc. 2008, 130, 15786.
186. e) M. Rueping, A. P. Antonchick, E. Sugiono, K. Grenader, Angew. Chem., Int. Ed. 2009, 48, 908.
187. C-O bond formation: f)G. Li, F. R. Fronczek, J. C. Antilla, J. Am. Chem. Soc. 2008, 130, 12216.
188. a) S. Xu, Z. Wang, X. Zhang, X. Zhang, K. Ding, Angew. Chem., Int. Ed. 2008, 47, 2840.
189. b) M. Lu, D. Zhu, Y. Lu, X. Zeng, B. Tan, Z. Xu, G. Zhong, J. Am. Chem. Soc. 2009, 131, 4562.
190. For recent examples of chiral Brønsted acid catalysts, see: a) M. Hatano, T. Maki, K. Moriyama, M. Arinobe, K. Ishihara, J. Am. Chem. Soc. 2008, 130, 16858.
191. b) C. Uyeda, E. N. Jacobsen, J. Am. Chem. Soc. 2008, 130, 9228.
192. c) P. Garcia-García, F. Lay, P. García-García, C. Rabalakos, B. List, Angew. Chem., Int. Ed. 2009, 48, 4363.
193. d) D. Uraguchi, D. Nakashima, T. Ooi, J. Am. Chem. Soc. 2009, 131, 7242.
194. T. Akiyama, T. Katoh, K. Mori, K. Kanno, Synlett 2009, 1664.