Recent advances in direct catalytic asymmetric transformations under proton-transfer conditions

Angewandte Chemie - International Edition

Volumn 50, Issue 21, 2011, Pages 4760-4772

  Kumagai, Naoya ^a   Shibasaki, Masakatsu ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

asymmetric catalysis; atom economy; cooperative effects; proton transfer; tetrasubstituted stereogenic centers

Indexed keywords

ASYMMETRIC CATALYSIS; ASYMMETRIC TRANSFORMATIONS; ATOM ECONOMY; C-C BOND FORMING REACTION; CATALYTIC ASYMMETRIC REACTIONS; CATALYTIC EFFICIENCIES; CHEMICAL ENTITY; COOPERATIVE CATALYSIS; COOPERATIVE EFFECTS; COOPERATIVITY; ENANTIOMERIC PURITY; MILD REACTION CONDITIONS; ORGANIC TRANSFORMATIONS; SPECIFIC INTERACTION; STEREO-SELECTIVE; STEREOSELECTIVE REACTIONS; SYNTHETIC STRATEGIES; TETRASUBSTITUTED STEREOGENIC CENTERS;

ATOMS; CATALYSIS; CHEMICAL BONDS; STEREOSELECTIVITY;

PROTONS;

CARBON; CYANIDE; IMINE; KETONE; LEWIS BASE; PROTON; SOLVENT;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CARBON; CATALYSIS; CYANIDES; IMINES; KETONES; LEWIS BASES; MOLECULAR STRUCTURE; PROTONS; SOLVENTS; STEREOISOMERISM;

EID: 79955751162     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100918     Document Type: Article

References (281)

1. Comprehensive Asymmetric Catalysis (Eds:, E.N. Jacobsen, A. Pfaltz, A.H. Yamamoto,), Berlin, Springer, 1999, and 2003 (For Supplement I)
2. Catalytic Asymmetric Synthesis (Ed.:, I. Ojima,) Wiley, New York, 2000
3. New Frontiers in Asymmetric Catalysis (Eds:, K. Mikami, K. Lautens,), Wiley, New York, 2007
4. P. J. Walsh, M. C. Kozlowski, Fundamentals of Asymmetric Catalysis, University Science Books, Sausalito, 2009
5. E. J. Corey, L. Kürti, Enantioselective Chemical Synthesis, Direct Book Publishing, Dallas, 2010.
6. Handbook of Green Chemistry-Green Catalysis (Eds.:, P.T. Anastas, R.H. Crabtree,), Wiley-VCH, Weinheim, 2009.
7. B. M. Trost, Science 1991, 254, 1471.
8. Enzyme Catalysis in Organic Synthesis (Eds.:, K. Drauz, H. Waldmann,), Wiley-VCH, Weinheim, 2002.
9. T. D. Machajewski, C.-H. Wang, Angew. Chem. 2009, 121, 1406-1430
10. Angew. Chem. Int. Ed. 2000, 39, 1352-1375.
11. For recent reviews on cooperative catalysis, see: Lewis acid/Brønsted base
12. M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187
13. S. Matsunaga, M. Shibasaki, Bull. Chem. Soc. Jpn. 2008, 81, 60. Lewis acid/Lewis base
14. M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491
15. D. H. Paull, C. J. Abraham, M. T. Scerba, E. Alden-Danforth, T. Lectka, Acc. Chem. Res. 2008, 41, 655. Lewis acid/Brønsted acid and Lewis acid/Lewis acid
16. H. Yamamoto, K. Futatsugi, Angew. Chem. 2005, 117, 1958
17. Angew. Chem. Int. Ed. 2005, 44, 1924
18. H. Yamamoto, K. Futatsugi, in Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008. Heterogeneous catalysis
19. J.-K. Lee, M. C. Kung, H. H. Kung, Top. Catal. 2008, 49, 136. Metal-organic cooperative catalysis
20. Y. J. Park, J.-W. Park, C.-H. Jun, Acc. Chem. Res. 2008, 41, 222.
21. J.-P. Genet, C. Greck, D. Lavergne, in Modern Amination Methods (Ed.:, A. Ricci,), Wiley-VCH, Weinheim, 2000, pp. 65-102
22. K. Krohn, in Organic Synthesis Highlights, Wiley-VCH, Weinheim, 1991, pp. 45-53.
23. T. Negoro, M. Murata, S. Ueda, B. Fujitani, Y. Ono, A. Kuromiya, M. Komiya, K. Suzuki, J.-I. Matsumoto, J. Med. Chem. 1998, 41, 4118
24. M. Kurono, I. Fujiwara, K. Yoshida, Biochemistry 2001, 40, 8216
25. V. Bril, R. A. Buchanan, Diabetes Care 2004, 27, 2369
26. M. Kurono, A. Fujii, M. Murata, B. Fujitani, T. Negoro, Biochem. Pharmacol. 2006, 71, 338
27. N. Giannoukakis, Curr. Opin. Invest. Drugs 2006, 7, 916
28. T. Matsumoto, Y. Ono, M. Kurono, A. Kuromiya, K. Nakamura, V. Bril, J. Pharmacol. Sci. 2008, 107, 231.
29. For general reviews, see
30. J.-P. Genet, C. Greck, Synlett 1997, 741
31. E. Erdik, Tetrahedron 2004, 60, 8747.
32. For reviews of catalytic asymmetric electrophilic amination of carbonyl compounds, see
33. R. O. Duthaler, Angew. Chem. 2003, 115, 1005
34. Angew. Chem. Int. Ed. 2003, 42, 975
35. C. Greck, B. Drouillat, C. Thomassigny, Eur. J. Org. Chem. 2004, 1377
36. J. M. Janey, Angew. Chem. 2005, 117, 4364
37. Angew. Chem. Int. Ed. 2005, 44, 4292
38. C. Cativiela, M. Ordõñez, Tetrahedron: Asymmetry 2009, 20, 1.
39. For the first examples of catalytic asymmetric α-amination of carbonyl compounds, see
40. D. A. Evans, S. G. Nelson, J. Am. Chem. Soc. 1997, 119, 6452
41. D. A. Evans, D. S. Johnson, Org. Lett. 1999, 1, 595.
42. For selected examples using metal-based catalysts, see
43. M. Marigo, K. Juhl, K. A. Jørgensen, Angew. Chem. 2003, 115, 1405
44. Angew. Chem. Int. Ed. 2003, 42, 1367
45. S. Ma, N. Jiao, Z. Zheng, Z. Ma, Z. Lu, L. Ye, Y. Deng, G. Chen, Org. Lett. 2004, 6, 2193
46. C. Foltz, B. Stecker, G. Marconi, S. Bellemin-Laponnaz, H. Wadepohl, L. H. Gabe, Chem. Commun. 2005, 5115
47. L. Bernardi, W. Zhuang, K. A. Jørgensen, J. Am. Chem. Soc. 2005, 127, 5772
48. Y. K. Kim, D. Y. Kim, Tetrahedron Lett. 2006, 47, 4565
49. J. Comelles, A. Pericas, M. Moreno-Mañas, A. Vallribera, G. Drudis-Solé, A. Lledos, T. Parella, A. Roglans, S. García-Granda, L. Roces-Fernández, J. Org. Chem. 2007, 72, 2077
50. Y. Hasegawa, M. Watanabe, I. D. Gridnev, T. Ikariya, J. Am. Chem. Soc. 2008, 130, 2158
51. J. Y. Mang, D. G. Kwon, D. Y. Kim, J. Fluorine Chem. 2009, 130, 259
52. T. Ikariya, I. D. Gridnev, Chem. Rec. 2009, 9, 106
53. Z. Yang, Z. Wang, S. Bai, K. Shen, D. Chen, X. Liu, L. Lin, X. Feng, Chem. Eur. J. 2010, 16, 6632.
54. For selected examples using organocatalysts, see
55. S. Saaby, M. Bella, K. A. Jørgensen, J. Am. Chem. Soc. 2004, 126, 8120
56. P. M. Pihko, A. Pohjakallio, Synlett 2004, 2115
57. X. Liu, X. Li, L. Deng, Org. Lett. 2005, 7, 167
58. X. Xu, T. Yabuta, P. Yuan, Y. Takemoto, Synlett 2006, 137
59. M. Terada, M. Nakano, H. Ube, J. Am. Chem. Soc. 2006, 128, 16044
60. Y. Liu, R. Melgar-Fernandez, E. Juaristi, J. Org. Chem. 2007, 72, 1522
61. S. H. Jung, D. Y. Kim, Tetrahedron Lett. 2008, 49, 5527
62. R. He, X. Wang, T. Hashimoto, K. Maruoka, Angew. Chem. 2008, 120, 9608
63. Angew. Chem. Int. Ed. 2008, 47, 9466
64. Q. Lan, X. Wang, R. He, C. Ding, K. Maruoka, Tetrahedron Lett. 2009, 50, 3280
65. X. Liu, B. Sun, L. Deng, Synlett 2009, 1685
66. L. Cheng, L. Liu, D. Wang, Y.-J. Chen, Org. Lett. 2009, 11, 3874
67. H. Konishi, T. Y. Lam, J. P. Malerich, V. H. Rawal, Org. Lett. 2010, 12, 2028.
68. R. Huisgen, F. Jakob, Justus Liebigs Ann. Chem. 1954, 590, 37; for electrophilic amination using azodicarboxylates, see
69. O. Diels, Justus Liebigs Ann. Chem. 1922, 429, 1
70. O. Diels, H. Behncke, Ber. Dtsch. Chem. Ges. 1924, 57, 653; for a general review of the use of azodicarboxylates in C-N bond-forming reactions, see
71. V. Nair, A. T. Biju, S. C. Mathew, B. P. Babu, Chem. Asian J. 2008, 3, 810.
72. T. Mashiko, K. Hara, D. Tanaka, Y. Fujiwara, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 11342.
73. For recent selected examples of small peptide-based asymmetric catalysis, see
74. Y. Zhao, J. Rodrigo, A. H. Hoveyda, M. C. Snapper, Nature 2006, 443, 67
75. C. A. Lewis, A. Chiu, M. Kubryk, J. Balsells, D. Pollard, C. K. Esser, J. Murry, R. A. Reamer, K. B. Hansen, S. J. Miller, J. Am. Chem. Soc. 2006, 128, 16454; for reviews, see
76. A. H. Hoveyda, A. W. Hird, M. A. Kacprzynski, Chem. Commun. 2004, 1779
77. J. T. Blank, S. J. Miller, Biopolymers 2006, 84, 38
78. E. A. ColbyDavie, S. M. Mennen, Y. Xu, S. J. Miller, Chem. Rev. 2007, 107, 5759.
79. Other examples of asymmetric catalysis using rare earth metal/amide-based ligand catalysts, see
80. A. Nishida, M. Yamanaka, M. Nakagawa, Tetrahedron Lett. 1999, 40, 1555
81. Y. Sudo, D. Shirasaki, S. Harada, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 12588.
82. For the other utilities of chiral ligand 5 a, see
83. A. Nojiri, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 5630
84. A. Nojiri, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 3779
85. Y. Kawato, N. Takahashi, N. Kumagai, M. Shibasaki, Org. Lett. 2010, 12, 1484
86. A. Matsuzawa, A. Nojiri, N. Kumagai, M. Shibasaki, Chem. Eur. J. 2010, 16, 5036.
87. 2O. Bulk purchase may even lower the cost. Sigma-Aldrich Handbook of Fine Chemicals, 2009-2010.
88. T. Mashiko, N. Kumagai, M. Shibasaki, Org. Lett. 2008, 10, 2725
89. M. Shibasaki, N. Kumagai, T. Mashiko, Curr. Opin. Drug Discov. Devel. 2009, 12, 862.
90. T. Watanabe, T. Kawabata, Heterocycles 2008, 76, 1593
91. B. M. Trost, M. Osipov, G. Dong, Org. Lett. 2010, 12, 1276.
92. For catalytic asymmetric fluorination of N-unsubstituted α-tert-butoxycarbonyl lactams, see
93. T. Suzuki, T. Oto, Y. Hamashima, M. Sodeoka, J. Org. Chem. 2007, 72, 246; for a partially successful 1,4-reduction of unsaturated primary amide and the subsequent enantioselective protonation by asymmetric catalysts (one example, 50 % ee), see
94. Y. Ohtsuka, T. Ikeno, T. Yamada, Tetrahedron: Asymmetry 2003, 14, 967; for a review of enzymatic kinetic resolution of primary amides, see
95. M.-X. Wang, Top. Catal. 2005, 35, 117, and references therein.
96. For diastereoselective reactions using α-alkoxycarbonyl amides not substituted at the nitrogen atom as substrates, see:, M. C. Kozlowski, E. S. DiVirgilio, K. Malolanarasimhan, C. A. Mulrooney, Tetrahedron: Asymmetry 2005, 16, 3599; for catalytic transformation such α-alkoxycarbonyl amides, see
97. J. Zhang, K. D. Sarma, T. T. Curran, D. T. Belmont, J. G. Davidson, J. Org. Chem. 2005, 70, 5890.
98. T. Mashiko, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 14990.
99. F. Berhal, S. Takechi, N. Kumagai, M. Shibasaki, Chem. Eur. J. 2011, 17, 1915.
100. Isolation and total synthesis of mycestericin F or G
101. T. Fujita, K. Inoue, S. Yamamoto, T. Ikumoto, S. Sasaki, R. Toyama, K. Chiba, Y. Hoshino, T. Okumoto, J. Antibiot. 1994, 47, 216
102. S. Sasaki, R. Hashimoto, M. Kiuchi, K. Inoue, T. Ikumoto, R. Hirose, K. Chiba, Y. Hoshino, T. Okumoto, T. Fujita, J. Antibiot. 1994, 47, 420
103. T. Fujita, N. Hamamichi, M. Kiuchi, T. Matsuzaki, Y. Kitao, K. Inoue, R. Hirose, M. Yoneta, S. Sasaki, K. Chiba, J. Antibiot. 1996, 49, 846
104. T. Fujita, N. Hamamichi, T. Matsuzaki, Y. Kitao, M. Kiuchi, M. Node, R. Hirose, Tetrahedron Lett. 1995, 36, 8599
105. K. Shibata, K. Shingu, V. P. Vassilev, K. Nishide, T. Fujita, M. Node, T. Kajimoto, C.-H. Wong, Tetrahedron Lett. 1996, 37, 2791.
106. L. Henry, C. R. Hebd. Seances Acad. Sci. 1895, 120, 1265; for recent general reviews on asymmetric nitroaldol reaction, see
107. F. A. Luzzio, Tetrahedron 2001, 57, 915
108. J. Boruwa, N. Gogoi, P. P. Saikia, N. C. Barua, Tetrahedron: Asymmetry 2006, 17, 3315
109. C. Palomo, M. Oiarbide, A. Laso, Eur. J. Org. Chem. 2007, 2561.
110. H. Sasai, T. Tokunaga, S. Watanabe, T. Suzuki, N. Itoh, M. Shibasaki, J. Org. Chem. 1995, 60, 7388.
111. Y. Sohtome, Y. Hashimoto, K. Nagasawa, Eur. J. Org. Chem. 2006, 2894
112. T. Arai, M. Watanabe, A. Yanagisawa, Org. Lett. 2007, 9, 3595
113. Y. Sohtome, N. Takemura, K. Takada, R. Takagi, T. Iguchi, K. Nagasawa, Chem. Asian J. 2007, 2, 1150
114. T. Arai, R. Takashita, Y. Endo, M. Watanabe, A. Yanagisawa, J. Org. Chem. 2008, 73, 4903; for partially successful examples of syn-selective catalytic asymmetric nitroaldol reaction, see
115. J. Yoshimoto, C. A. Sandoval, S. Saito, Chem. Lett. 2008, 37, 1294
116. H. Y. Kim, K. Oh, Org. Lett. 2009, 11, 5682.
117. For anti-selective nitroaldol reaction of silyl nitronates, see
118. D. Seebach, A. K. Beck, T. Mukhopadhyay, E. Thomas, Helv. Chim. Acta 1982, 65, 1101; for anti-selective catalytic asymmetric nitroaldol reaction using silyl nitronates, see
119. T. Risgaard, K. V. Gothelf, K. A. Jørgensen, Org. Biomol. Chem. 2003, 1, 153
120. T. Ooi, K. Doda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 2054.
121. For partially successful examples of anti-selective catalytic asymmetric nitroaldol reaction, see
122. G. Blay, L. R. Domingo, V. Hernández-Olmos, J. R. Pedro, Chem. Eur. J. 2008, 14, 4725
123. H. Ube, M. Terada, Bioorg. Med. Chem. Lett. 2009, 19, 3895
124. A. Noole, K. Lippur, A. Metsala, M. Lopp, T. Kanger, J. Org. Chem. 2010, 75, 1313
125. G. Blay, V. Hernández-Olmos, J. R. Pedro, Org. Lett. 2010, 12, 3058; for anti-selective nitroaldol reaction of benzaldehyde catalyzed by hydroxynitrile lyase, see
126. T. Purkarthofer, K. Gruber, M. Gruber-Khadjawi, K. Waich, W. Skranc, D. Mink, H. Griengl, Angew. Chem. 2006, 118, 3532
127. Angew. Chem. Int. Ed. 2006, 45, 3454
128. M. Gruber-Khadjawi, T. Purkarthofer, W. Skranc, H. Griengl, Adv. Synth. Catal. 2007, 349, 1445.
129. D. Uraguchi, S. Sakaki, T. Ooi, J. Am. Chem. Soc. 2007, 129, 12392.
130. D. Uraguchi, S. Nakamura, T. Ooi, Angew. Chem. 2010, 122, 7724
131. Angew. Chem. Int. Ed. 2010, 49, 7562.
132. S. F. Matkhalikova, V. M. Malikov, S. Y. Yunusov, Khim. Prir. Soedin. 1969, 5, 30
133. S. F. Matkhalikova, V. M. Malikov, S. Y. Yunusov, Khim. Prir. Soedin. 1969, 5, 606.
134. For a review, see:, M. Shibasaki, S. Matsunaga, J. Synth. Org. Chem. Jpn. 2010, 68, 1142.
135. For related attempts to develop bifunctional asymmetric catalysts using heterodinuclear Schiff base complexes, see
136. V. Annamalai, E. F. DiMauro, P. J. Carroll, M. C. Kozlowski, J. Org. Chem. 2003, 68, 1973
137. G. M. Sammis, H. Danjo, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 9928
138. W. Li, S. S. Thakur, S.-W. Chen, C.-K. Shin, R. B. Kawthekar, G.-J. Kim, Tetrahedron Lett. 2006, 47, 3453, and references therein.
139. S. Handa, K. Nagawa, Y. Sohtome, S. Matsunaga, M. Shibasaki, Angew. Chem. 2008, 120, 3274
140. Angew. Chem. Int. Ed. 2008, 47, 3230.
141. For reviews of bimetallic cooperative catalysis, see
142. Multimetallic Catalysis in Organic Synthesis (Eds.:, M. Shibasaki, Y. Yamamoto,), Wiley-VCH, Weinheim, 2004
143. M. Shibasaki, S. Matsunaga, Chem. Soc. Rev. 2006, 35, 269
144. M. Shibasaki, M. Kanai, Org. Biomol. Chem. 2007, 5, 2027.
145. N. Yamazaki, Y. Fukuda, Y. Shibazaki, T. Niizato, I. Kosugi, S. Yoshioka, US Patent 5,449,694, 1995.
146. N. Tanaka, T. Tamai, H. Mukaiyama, A. Hirabayashi, H. Muranaka, M. Sato, M. Akahane, Patent WO00/02846, 1999.
147. T. Nitabaru, N. Kumagai, M. Shibasaki, Tetrahedron Lett. 2008, 49, 272
148. T. Nitabaru, A. Nojiri, M. Kobayashi, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 13860.
149. C. Li, Y.-Y. Zhu, H.-P. Yi, C.-Z. Li, X.-K. Jiang, Z.-T. Li, Y.-H. Yu, Chem. Eur. J. 2007, 13, 9990
150. K. Tomita, S. Oishi, H. Ohno, N. Fujii, Biopolymers 2008, 90, 503, and references therein.
151. For reviews of chiral catalysts incorporated into metal-organic coordination frameworks, see
152. A. Baiker, J. Mol. Catal. A 1997, 115, 473
153. O. M. Yaghi, H. Li, C. Davis, D. Richardson, T. L. Groy, Acc. Chem. Res. 1998, 31, 474
154. P. J. Hagrman, D. Hagrman, J. Zubieta, Angew. Chem. 1999, 111, 2798
155. Angew. Chem. Int. Ed. 1999, 38, 2638
156. A. J. Blake, N. R. Champness, P. Hubberstey, W.-S. Li, M. A. Withersby, M. Schroder, Coord. Chem. Rev. 1999, 183, 117
157. B. Moulton, M. J. Zaworotko, Chem. Rev. 2001, 101, 1629
158. B. Kesanli, W. B. Lin, Coord. Chem. Rev. 2003, 246, 305
159. M. Studer, H. U. Blaser, C. Exner, Adv. Synth. Catal. 2003, 345, 45
160. O. M. Yaghi, M. O'Keeffe, N. W. Ockwig, H. K. Chae, M. Eddaoudy, J. Kim, Nature 2003, 423, 715
161. L. X. Dai, Angew. Chem. 2004, 116, 5846
162. Angew. Chem. Int. Ed. 2004, 43, 5726
163. T. Mallat, E. Orglmeister, A. Baiker, Chem. Rev. 2007, 107, 4863. For selected leading examples of "self-supported" chiral catalysts comprising metal-organic coordination networks, see
164. T. Sawaki, Y. Aoyama, J. Am. Chem. Soc. 1999, 121, 4793
165. J. S. Seo, D. Whang, H. Lee, S. I. Jun, J. Oh, Y. J. Jeon, K. A. Kim, Nature 2000, 404, 982
166. A. Hu, H. L. Ngo, W. Lin, J. Am. Chem. Soc. 2003, 125, 114900
167. S. Takizawa, H. Somei, D. Jayaprakash, H. Sasai, Angew. Chem. 2003, 115, 5889
168. Angew. Chem. Int. Ed. 2003, 42, 5711
169. H. Guo, X. Wang, K. Ding, Tetrahedron Lett. 2004, 45, 2009
170. Y. Liang, Q. Jing, X. Li, L. Shi, K. Ding, J. Am. Chem. Soc. 2005, 127, 7694.
171. Selected early examples of direct catalytic asymmetric aldol reactions, see
172. Y. M. A. Yamada, N. Yoshikawa, H. Sasai, M. Shibasaki, Angew. Chem. 1997, 109, 1942
173. Angew. Chem. Int. Ed. Engl. 1997, 36, 1871
174. N. Yoshikawa, Y. M. A. Yamada, J. Das, H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 1999, 121, 4168
175. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395
176. B. M. Trost, H. Ito, J. Am. Chem. Soc. 2000, 122, 12003
177. R. Mahrwald, B. Ziemer, Tetrahedron Lett. 2002, 43, 4459.
178. For reviews of direct catalytic asymmetric aldol reactions, see
179. B. Alcaide, P. Almendros, Eur. J. Org. Chem. 2002, 1595
180. W. Notz, F. Tanaka, C. F. Barbas III, Acc. Chem. Res. 2004, 37, 580
181. Modern Aldol Reactions (Ed.:, R. Mahrwald,), Wiley-VCH, Berlin, 2004
182. S. Mukherjee, W. J. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471
183. B. M. Trost, C. S. Brindle, Chem. Soc. Rev. 2010, 39, 1600.
184. E. J. Corey, A. Guzman-Perez, Angew. Chem. 1998, 110, 402
185. Angew. Chem. Int. Ed. 1998, 37, 388
186. J. Christoffers, A. Mann, Angew. Chem. 2001, 113, 4725
187. Angew. Chem. Int. Ed. 2001, 40, 4591
188. C. J. Douglas, L. E. Overman, Proc. Natl. Acad. Sci. USA 2004, 101, 5363
189. B. M. Trost, C. Jiang, Synthesis 2006, 369
190. P. G. Cozzi, R. Hilgraf, N. Zimmermann, Eur. J. Org. Chem. 2007, 5969
191. M. Bella, T. Gasperi, Synthesis 2009, 1583.
192. S. Arseniyadis, K. S. Kyler, D. S. Watt, Org. React. 1984, 31, 1
193. F. F. Fleming, P. S. Iyer, Synthesis 2006, 893.
194. N. Kumagai, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 13632
195. L. Fan, O. V. Ozerov, Chem. Commun. 2005, 4450
196. A. Goto, K. Endo, Y. Ukai, S. Irle, S. Saito, Chem. Commun. 2008, 2212.
197. For examples for the use of allylic cyanides as pronucleophiles in racemic reactions, see
198. P. B. Kisanga, J. G. Verkade, J. Org. Chem. 2002, 67, 426
199. J. Aydin, K. J. Szabõ, Org. Lett. 2008, 10, 2881.
200. For recent reviews, see
201. O. Riant, J. Hannedouche, Org. Biomol. Chem. 2007, 5, 873
202. M. Kanai, M. Shibasaki, Chem. Rev. 2008, 108, 2853.
203. P. Vachal, E. N. Jacobsen, Org. Lett. 2000, 2, 867
204. P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012
205. M. Rueping, E. Sugiono, S. A. Moreth, Adv. Synth. Catal. 2007, 349, 759.
206. W. Zhuang, S. Saaby, K. A. Jørgensen, Angew. Chem. 2004, 116, 4576
207. Angew. Chem. Int. Ed. 2004, 43, 4476.
208. For a review, see:, S. M. Weinreb, R. K. Orr, Synthesis 2005, 1205.
209. R. Yazaki, T. Nitabaru, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2008, 130, 14477.
210. For selected examples of catalytic asymmetric C-C bond formation using Cu alkoxides, see
211. J. Krüger, E. M. Carreira, J. Am. Chem. Soc. 1998, 120, 837
212. B. L. Pagenkopf, J. Krüger, A. Stojanovic, E. M. Carreira, Angew. Chem. 1998, 110, 3312
213. Angew. Chem. Int. Ed. 1998, 37, 3124
214. Y. Suto, R. Tsuji, M. Kanai, M. Shibasaki, Org. Lett. 2005, 7, 3757
215. R. Wada, T. Shibuguchi, S. Makino, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 7687
216. R. Motoki, M. Kanai, M. Shibasaki, Org. Lett. 2007, 9, 2997
217. Y. Asano, K. Hara, H. Ito, M. Sawamura, Org. Lett. 2007, 9, 3901.
218. For a partially successful example (moderate yield, long reaction time) of catalytic asymmetric aza-Henry reaction of nitromethane and N-tosyl ketoimines under proton-transfer conditions, see:, C. Tan, X. Liu, L. Wang, J. Wang, X. Feng, Org. Lett. 2008, 10, 5305. During the review of this manuscript, catalytic asymmetric nitroaldol reaction of trifluoromethylketones was reported, see
219. C. Palacio, S. J. Connon, Org. Lett. 2011, 13, 1298.
220. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 3195.
221. For examples of catalytic asymmetric addition to ketones coupled with hydrogenation, see
222. H. W. Lam, P. M. Joensuu, Org. Lett. 2005, 7, 4225
223. J.-R. Kong, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 718
224. J. Deschamp, O. Chuzel, J. Hannedouche, O. Riant, Angew. Chem. 2006, 118, 1314
225. Angew. Chem. Int. Ed. 2006, 45, 1292
226. V. Komanduri, M. J. Krische, J. Am. Chem. Soc. 2006, 128, 16448
227. T. Shiomi, H. Nishiyama, Org. Lett. 2007, 9, 1651
228. J. F. Bower, I. S. Kim, R. L. Patman, M. J. Krische, Angew. Chem. 2009, 121, 36
229. Angew. Chem. Int. Ed. 2009, 48, 34.
230. A. Chmura, G. M. vanderKraan, L. M. vanLangen, F. vanRantwijk, R. A. Sheldon, Adv. Synth. Catal. 2006, 348, 1655
231. J. vonLangermann, A. Mell, E. Paetzold, T. Daußmann, U. Kragl, Adv. Synth. Catal. 2007, 349, 1418
232. S. J. Zuend, E. N. Jacobsen, J. Am. Chem. Soc. 2007, 129, 15872.
233. For recent reviews on catalytic asymmetric synthesis of tertiary alcohols, see
234. J. Christoffers, A. Baro, Angew. Chem. 2003, 115, 1726
235. Angew. Chem. Int. Ed. 2003, 42, 1688
236. M. Hatano, K. Ishihara, Synthesis 2008, 1647
237. B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963
238. S. Adachi, T. Harada, Eur. J. Org. Chem. 2009, 3661; for a general and efficient protocol for the synthesis of enantioenriched tertiary alcohols, see
239. J. L. Stymiest, V. Bagutski, R. M. French, V. K. Aggarwal, Nature 2008, 456, 778.
240. M. Hatano, E. Takagi, K. Ishihara, Org. Lett. 2007, 9, 4527.
241. R. Yazaki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2010, 132, 5522.
242. For a comprehensive review of Lewis base catalysis, see
243. S. E. Denmark, G. L. Beutner, Angew. Chem. 2008, 120, 1584
244. Angew. Chem. Int. Ed. 2008, 47, 1560, and references therein.
245. For direct catalytic asymmetric aldol (-type) reactions using aldol donors at the carboxylic acid oxidation state without electron-withdrawing α-substituents: alkyl nitriles: ref.[55c]; activated amides
246. S. Saito, S. Kobayashi, J. Am. Chem. Soc. 2006, 128, 8704; β,γ-unsaturated ester
247. A. Yamaguchi, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 10842; 5H-oxazol-4-ones
248. T. Misaki, G. Takimoto, T. Sugimura, J. Am. Chem. Soc. 2010, 132, 6286; direct catalytic asymmetric aldol reaction of thiazolidinethiones where the use of a stoichiometric amount of silylating reagent was essential
249. D. A. Evans, C. W. Downey, J. L. Hubbs, J. Am. Chem. Soc. 2003, 125, 8706.
250. T. S. Jagodziński, Chem. Rev. 2003, 103, 197, and references therein.
251. For selected example of the use of thioamide as pronucleophile in diastereoselective C-C bond-forming reactions with stoichiometric amount of reagents, see
252. Y. Tamaru, T. Harada, S. Nishi, M. Mizutani, T. Hioki, Z. Yoshida, J. Am. Chem. Soc. 1980, 102, 7806
253. C. Goasdoue, N. Goasdoue, M. Gaudemar, M. Mladenova, J. Organomet. Chem. 1981, 208, 279.
254. N. Iwasawa, T. Yura, T. Mukaiyama, Tetrahedron 1989, 45, 1197.
255. For reviews of direct Mannich(-type) reactions, see
256. M. M. B. Marques, Angew. Chem. 2006, 118, 356
257. Angew. Chem. Int. Ed. 2006, 45, 348
258. A. Ting, S. E. Schaus, Eur. J. Org. Chem. 2007, 5797
259. J. M. M. Verkade, L. J. C. vanHemert, P. J. L. M. Quaedflieg, F. P. J. T. Rutjes, Chem. Soc. Rev. 2008, 37, 29. For general reviews on catalytic asymmetric Mannich reactions, see
260. S. Kobayashi, M. Ueno, in Comprehensive Asymmetric Catalysis, Supplement 1 (Eds.:, E.N. Jacobsen, A. Pfaltz, H. Yamamoto,), Springer, Berlin, 2003, chap. 29.5, p. 143
261. G. Friestad, A. K. Mathies, Tetrahedron 2007, 63, 2541.
262. N. Utsumi, S. Kitagaki, C. F. Barbas III, Org. Lett. 2008, 10, 3408.
263. Y. Suzuki, R. Yazaki, N. Kumagai, M. Shibasaki, Angew. Chem. 2009, 121, 5126
264. Angew. Chem. Int. Ed. 2009, 48, 5026.
265. S. Kobayashi, H. Kiyohara, M. Yamaguchi, J. Am. Chem. Soc. 2011, 133, 708.
266. There are numerous examples of direct aldol reactions using aldol donors bearing electron-withdrawing α-substituents that are readily enolized under mild basic conditions. For pioneering work using α-isocyanoacetates, see:, H. Ito, M. Sawamura, T. Hayashi, J. Am. Chem. Soc. 1986, 108, 6405.
267. M. Iwata, R. Yazaki, Y. Suzuki, N. Kumagai, M. Shibasaki, J. Am. Chem. Soc. 2009, 131, 18244
268. M. Iwata, R. Yazaki, N. Kumagai, M. Shibasaki, Tetrahedron: Asymmetry 2010, 21, 1688.
269. For reviews, see
270. S. Masamune, W. Choy, Aldrichimica Acta 1982, 15, 47
271. T. Oishi, T. Nakata, Synthesis 1990, 635
272. C. S. Poss, S. L. Schreiber, Acc. Chem. Res. 1994, 27, 9
273. C. Schneider, Angew. Chem. 1998, 110, 1445
274. Angew. Chem. Int. Ed. 1998, 37, 1375
275. S. E. Bode, M. Wolberg, M. Müller, Synthesis 2006, 557.
276. For recent selected examples of the stereoselective synthesis of 1,3-polyols via catalytic asymmetric C-C bond formation, see
277. S. Chandrasekhar, C. Narsihmulu, S. S. Sultana, M. S. Reddy, Tetrahedron Lett. 2004, 45, 9299
278. Z. Zhang, S. Aubry, Y. Kishi, Org. Lett. 2008, 10, 3077
279. Y. Lu, I. S. Kim, A. Hassan, D. J. DelValle, M. J. Krische, Angew. Chem. 2009, 121, 5118
280. Angew. Chem. Int. Ed. 2009, 48, 5018
281. A. Hassan, Y. Lu, M. J. Krische, Org. Lett. 2009, 11, 3112.