Asymmetric Oxidations and Related Reactions

Catalytic Asymmetric Synthesis: Third Edition

Volumn , Issue , 2010, Pages 839-890

  Matsumoto, Kazuhiro ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Asymmetric oxidations and related reactions; Chiral lanthanoid based complexes versatile catalysts for enantioselective organic transformations; Phase transfer catalysis methodology for organic synthesis under aqueous conditions

Indexed keywords

EID: 84886082156     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470584248.ch11     Document Type: Chapter

References (251)

1. (a) Comprehensive Organic Synthesis, Vol. 7 (Eds. Trost, B. M.; Fleming, I.). Oxford, Pergamon Press, 1991.
2. (b) Modern Oxidation Methods (Ed. Bäckval, J.-E.). Weinheim: Wiley- VCH, 2004.
3. (a) Trost, B. M. Science 1991, 254, 1471-1477.
4. (b) Trost, B. M. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281.
5. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457-2473.
6. Tojo, G.; Fernández, M. Oxidation of Alcohols to Aldehydes and Ketones. New York: Springer, 2006.
7. (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Gautier, A.; Dumeunier, R.; Doda, K.; Philippart, F.; Chellé-Regnault, I.; Mutonkole, J.-L.; Brown, S. M.; Urch, C. J. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 437-478.
8. (b) Schultz. M. J.; Sigman, M. S. Tetrahedron 2006, 62, 8227-8241.
9. (c) Sheldon, R. A.; Arends, I. W. C. E.; Dijksman, A. Catal. Today 2000, 57, 157-166.
10. Blackburn, T. F.; Schwartz, J. J. Chem. Soc., Chem. Commun. 1977, 157-158.
11. (a) Muzart, J. Tetrahedron 2003, 59, 5789-5816.
12. (b) Stahl, S. S. Angew. Chem. Int. Ed. 2004, 43, 3400-3420.
13. (c) Nielsen, R. J.; Keith, J. M.; Stoltz, B. M.; Goddard, W. A. III. J. Am. Chem. Soc. 2004, 126, 7967-7974.
14. (d) Zierkiewicz, W.; Privalov, T. Organometallics 2005, 24, 6019-6028.
15. (e) Gligorich, K. M.; Sigman, M. S. Angew. Chem. Int. Ed. 2006, 45, 6612-6615.
16. (f) Sigman, M. S.; Jensen, D. R. Acc. Chem. Res. 2006, 39, 221-229.
17. (g) Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348-4355.
18. (a) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011-6014.
19. (b) Peterson, K. P.; Larock, R. C. J. Org. Chem. 1998, 63, 3185-3189.
20. (c) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636-1639.
21. (d) Iwasawa, T.; Tokunaga, M.; Ohbora, Y.; Tsuji, Y. J. Am. Chem. Soc. 2004, 126, 6554-6555.
22. (e) Schultz, M. J.; Hamilton, S. S.; Jensen, D. R.; Sigman, M. S. J. Org. Chem. 2005, 70, 3343-3352.
23. Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475-7476.
24. Ferreira, E. M.; Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725-7726.
25. Mueller, J. A.; Jensen, D. R.; Sigman, M. S. J. Am. Chem. Soc. 2002, 124, 8202-8203.
26. Jensen, D. R.; Sigman, M. S. Org. Lett. 2003, 5, 63-65.
27. Mandal, S. K.; Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Org. Chem. 2003, 68, 4600-4603.
28. Bagdanoff, J. T.; Ferreira, E. M.; Stoltz, B. M. Org. Lett. 2003, 5, 835-837.
29. Bagdanoff, J. T.; Stoltz, B. M. Angew. Chem. Int. Ed. 2004, 43, 353-357.
30. Caspi, D. D.; Ebner, D. C.; Bagdanoff, J. T.; Stoltz, B. M. Adv. Synth. Catal. 2004, 346, 185-189.
31. Tambar, U. K.; Ebner, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 11752-11753.
32. (a) Markó, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661-12662.
33. (b) Lenz, R.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 3291-3292.
34. (c) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557-5560.
35. (d) Lee, M.; Chang, S. Tetrahedron Lett. 2000, 41, 7507-7510.
36. (e) Dijksman, A.; Marino-González, A.; Mairata, I.; Payeras, A.; Arends, I. W. C. E.; Sheldon, R. A. J. Am. Chem. Soc. 2001, 123, 6826-6833.
37. (f) Miyata, A.; Furukawa, M.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2002, 43, 3481-3484.
38. Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119-5123.
39. Nakamura, Y.; Egami, H.; Matsumoto, K.; Uchida, T.; Katsuki, T. Tetrahedron 2007, 63, 6383-6387.
40. (a) Shimizu, H.; Nakata, K.; Katsuki, T. Chem. Lett. 2002, 31, 1080-1081.
41. (b) Shimizu, H.; Katsuki, T. Chem. Lett. 2003, 32, 480-481.
42. Shimizu, H.; Onitsuka, S.; Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2005, 127, 5396-5413.
43. Wang, Y.; DuBois, J. L.; Hedman, B.; Hodgson, K. O.; Stack, T. D. P. Science 1998, 279, 537-540.
44. (a) Kirihara, M.; Ochiai, Y.; Takizawa, S.; Takahata, H.; Nemoto, H. Chem. Commun. 1999, 1387-1388.
45. (b) Maeda, Y.; Kakiuchi, N.; Matsumura, S.; Nishimura, T.; Uemura, S. Tetrahedron Lett. 2001, 42, 8877-8879.
46. (c) Maeda, Y.; Kakiuchi, N.; Matsumura, S.; Nishimura, T.; Kawamura, T.; Uemura, S. J. Org. Chem. 2002, 67, 6718-6724.
47. (d) Velusamy, S.; Punniyamurthy, T. Org. Lett. 2004, 6, 217-219.
48. Radosevich, A. T.; Musich, C.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 1090-1091.
49. Weng, S.-S.; Shen, M.-W.; Kao, J.-Q.; Munot, Y. S.; Chen, C.-T. Proc. Natl. Acad. Sci. USA 2006, 103, 3522-3527.
50. Pawar, V. D.; Bettigeri, S.; Weng, S.-S.; Kao, J.-Q.; Chen, C.-T. J. Am. Chem. Soc. 2006, 128, 6308-6309.
51. Radosevich, A. T.; Chan, V. S.; Shih, H.-W.; Toste, F. D. Angew. Chem. Int. Ed. 2008, 47, 3755-3758.
52. Arita, S.; Koike, T.; Kayaki, Y.; Ikariya, T. Angew. Chem. Int. Ed. 2008, 47, 2447-2449.
53. (a) Heiden, Z. M.; Rauchfuss, T. B. J. Am. Chem. Soc. 2007, 129, 14303-14310.
54. (b) Arita, S.; Koike, T.; Kayaki, Y.; Ikariya, T. Chem Asian J. 2008, 3, 1479-1485.
55. (a) Ikariya, T.; Blacker, A. J. Acc. Chem. Res. 2007, 40, 1300-1308.
56. (b) Ikariya, T; Murata, K.; Noyori, R. Org. Bio. Chem. 2006, 4, 393-406.
57. (c) Gladiali, S.; Alberico, E. Chem. Soc. Rev. 2006, 35, 226-236.
58. (d) Samec, J. S.; Bäckvall, J.-E.; Andersson, P. G.; Brandt, P. Chem. Soc. Rev. 2006, 35, 237-248.
59. (a) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
60. (b) Katsuki, T.; Martin, V. S. Org. Rect. 1996, 48, 1-299.
61. (a) Katsuki, T. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 621-648.
62. (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 649-677.
63. (c) Aggarwal, V. K. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 679-693.
64. (d) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.). New York: Wiley-VCH, 2000; pp. 231-280.
65. (e) Katsuki, T. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.). New York: Wiley-VCH, 2000; pp. 287-325.
66. (f) Berkessel, A. In Asymmetric Synthesis-The Essentials. (Eds. Christmann, M.; Bräse, S.). Weinheim: Wiley-VCH, 2007; pp. 176-180.
67. (g) Porter, M. J.; Skidmore, J. Chem. Commun. 2000, 1215-1225.
68. Tse, M. K.; Döbler, C.; Bhor, S.; Klawonn, M.; Mägerlein, W.; Hugl, H.; Beller, M. Angew. Chem. Int. Ed. 2004, 43, 5255-5260.
69. (a) Tse, M. K.; Bhor, S.; Klawonn, M.; Anilkumar, G.; Jiao, H.; Döbler, C.; Spannenberg, A.; Mägerlein, W.; Hugl, H.; Beller, M. Chem. Eur. J. 2006, 12, 1855-1874.
70. (b) Tse, M. K.; Bhor, S.; Klawonn, M.; Anilkumar, G.; Jiao, H.; Spannenberg, A.; Döbler, C.; Mägerlein, W.; Hugl, H.; Beller, M. Chem. Eur. J. 2006, 12, 1875-1888.
71. Nishiyama, H.; Shimada, T.; Itoh, H.; Sugiyama, H.; Motoyama, Y. Chem. Commun. 1997, 1863-1864.
72. Matsumoto, K.; Sawada, Y.; Saito, B.; Sakai, K.; Katsuki, T. Angew. Chem. Int. Ed. 2005, 44, 4935-4939.
73. Sawada, Y.; Matsumoto, K.; Katsuki, T. Angew. Chem. Int. Ed. 2007, 46, 4559-4561.
74. Sawada, Y.; Matsumoto, K.; Kondo, S.; Watanabe, H.; Ozawa, T.; Suzuki, K.; Saito, B.; Katsuki, T. Angew. Che. Int. Ed. 2006, 45, 3478-3480.
75. Matsumoto, K.; Sawada, Y.; Katsuki, T. Synlett 2006, 3545-3547.
76. Shimada, Y.; Kondo, Y.; S.; Ohara, Matsumoto, K.; Katsuki, T. Synlett 2007, 2445-2447.
77. Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2006, 128, 14006-14007.
78. Colladon, M.; Scarso, A.; Strukul, G. Adv. Synth. Catal. 2007, 349, 797-801.
79. Colladon, M.; Scarso, A.; Sgarbossa, P.; Michelin, R. A.; Strukul, G. J. Am. Chem. Soc. 2007, 129, 7680-7689.
80. (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217-6254.
81. (b) Enthaler, S.; Junge, K.; Beller, M. Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
82. Francis, M. B.; Jacobsen, E. N. Angew. Chem. Int. Ed. 1999, 38, 937-941.
83. Costas, M.; Tipton, A. K.; Chen, K.; Jo, D.-H.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 6722-6723.
84. Gelalcha, F. G.; Bitterlich, B.; Anikumar, G.; Tse, M. K.; Beller, M. Angew. Chem. Int. Ed. 2007, 46, 7293-7296.
85. Gelalcha, F. G.; Anikumar, G.; Tse, M. K.; Brückner, A.; Beller, M. Chem. Eur. J. 2008, 14, 7687-7698.
86. Adam, W.; Wirth, T. Acc. Chem. Res. 1999, 32, 703-710.
87. Rossiter, B. E.; Verhoeven, T. R.; Sharpless, K. B. Tetrahedron Lett. 1979, 20, 4733-4736.
88. (a) Michaelson, R. C.; Palermo, R. E.; Sharpless, K. B. J. Am. Chem. Soc. 1977, 99, 1990-1992.
89. (b) Sharpless, K. B.; Verhoeven, T. R. Aldrichim. Acta 1979, 12, 63-73.
90. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem. Int. Ed. 1995, 34, 1059-1070.
91. Bolm, C. Coord. Chem. Rev. 2003, 237, 245-256.
92. Murase, N.; Hoshino, Y.; Oishi, M.; Yamamoto, H. J. Org. Chem. 1999, 64, 338-339.
93. Hoshino, Y.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10452-10453.
94. Zhang, W.; Basak, A.; Kosugi, Y.; Hoshino, Y.; Yamamoto, H. Angew. Chem. Int. Ed. 2005, 44, 4389-4391.
95. Zhang, W.; Yamamoto, H. J. Am. Chem. Soc. 2007, 129, 286-287.
96. Egami, H.; Katsuki, T. Angew. Chem. Int. Ed. 2008, 47, 5171-5174.
97. Barlan, A. U.; Basak, A.; Yamamoto, H. Angew. Chem. Int. Ed. 2006, 45, 5849-5852.
98. (a) Yamada, S.; Mashiko, T.; Terashima, S. J. Am. Chem. Soc. 1977, 99, 1988-1990.
99. (b) Kühn, F. E.; Zhao, J.; Herrmann, W. A. Tetrahedron: Asymmetry 2005, 16, 3469-3479.
100. Basak, A.; Barlan, A. U.; Yamamoto, H. Tetrahedron: Asymmetry 2006, 17, 508-511.
101. (a) Bougauchi, M.; Watanabe, S.; Arai, T.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 2329-2330.
102. (b) Watanabe, S.; Kobayashi, Y.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 7353-7356.
103. (c) Nemoto, T.; Ohshima, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2725-2732.
104. (d) Nemoto, T.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 9474-9475.
105. (e) Nemoto, T.; Kakei, H.; Gnanadesikan, V.; Tosaki, S.-Y.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2002, 124, 14544-14545.
106. (f) Matsunaga, S.; Kinoshita, T.; Okada, S.; Harada, S.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 7559-7570.
107. (g) Tosaki, S.-Y.; Tsuji, R.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 2147-2155.
108. (h) Kakei, H.; Tsuji, R.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 8962-8963.
109. Daikai, K.; Kamaura, M.; Inanaga, J. Tetrahedron Lett. 1998, 39, 7321-7322.
110. Hara, K.; Park, S.-Y.; Yamagiwa, N.; Matsunaga, S.; Shibasaki, M. Chem. Asian J. 2008, 3, 1500-1504.
111. Nemoto, T.; Ohshima, T.; Shibasaki, M. Tetrahedron 2003, 59, 6889-6897.
112. Berkessel, A.; Gröger, H. Asymmetric Organocatalysis. Weinheim: Wiley-VCH, 2005.
113. (a) Curci, R.; Fiorentino, M.; Serio, M. R. J. Chem. Soc., Chem. Commun. 1984, 155-156.
114. (b) Curci, R.; D'Accolti, L.; Fiorentino, M.; Rosa, A. Tetrahedron Lett. 1995, 36, 5831-5834.
115. (a) Shi, Y. Acc. Chem. Res. 2004, 37, 488-496.
116. (b) Yang, D. Acc. Chem. Res. 2004, 37, 497-505.
117. (a) Tu, Y.; Wang, Z.-X.; Shi, Y. J. Am. Chem. Soc. 1996, 118, 9806-9807.
118. (b) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224-11235.
119. (a) Tian, H.; She, X.; Shu, L.; Yu, H.; Shi, Y. J. Am. Chem. Soc. 2000, 122, 11551-11552.
120. (b) H.; Tian, X.; She, J.; Xu, Shi, Y. Org. Lett. 2001, 3, 1929-1931.
121. (b) Tian, H.; She, X.; Yu, H.; Shu, L.; Shi, Y. J. Org. Chem. 2002, 67, 2435-2446.
122. Hickey, M.; Goeddel, D.; Crane, Z.; Shi, Y. Proc. Natl. Acad. Sci. USA 2004, 101, 5794-5798.
123. (a) Shu, L.; Wang, P.; Gan, Y.; Shi, Y. Org. Lett. 2003, 5, 293-296.
124. (b) Goeddel, D.; Shu, L.; Yuan, Y.; Wong, O. A.; Wang, B.; Shi, Y. J. Org. Chem. 2006, 71, 1715-1717.
125. Wu, X.-Y.; She, X.; Shi, Y. J. Am. Chem. Soc. 2002, 124, 8792-8793.
126. (a) Shen, Y.-M.; Wang, B.; Shi, Y. Angew. Chem. Int. Ed. 2006, 45, 1429-1432.
127. (b) Shen, Y.-M.; Wang, B.; Shi, Y. Tetrahedron Lett. 2006, 47, 5455-5458.
128. Trost, B. M.; Bogdanowicz, M. J. J. Am. Chem. Soc. 1972, 94, 4777-4779.
129. (a) Shu, L.; Shi, Y. Tetrahedron Lett. 1999, 40, 8721-8724.
130. (b) Shu, L.; Shi, Y. J. Org. Chem. 2000, 65, 8807-8810.
131. (c) Shu L.; Shi, Y. Tetrahedron 2001, 57, 5213-5218.
132. (d) Burke, C. P.; Shu, L.; Shi, Y. J. Org. Chem. 2007, 72, 6320-6323.
133. Peris, G.; Jakobsche, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 8710-8711.
134. Miller, S. J. Acc. Chem. Res. 2004, 37, 601-610.
135. (a) List, B. Chem. Commun. 2006, 819-824.
136. (b) Erkkilä, A.; Majander, L.; Pihko, P. M. Chem. Rev. 2007, 107, 5416-5470.
137. (c) Mukherjee, S.; Yang, J. W.; Hoffmann, S.; List, B. Chem. Rev. 2007, 107, 5471-5569.
138. Marigo, M.; Franzén, J.; Poulsen, T. B.; Zhuang, W.; Jørgensen, K. A. J. Am. Chem. Soc. 2005, 127, 6964-6965.
139. Zhuang, W.; Marigo, M.; Jørgensen, K. A. Org. Biomol Chem. 2005, 3, 3883-3885.
140. Sundén, H.; Ibrahem, I.; Córdova, A. Tetrahedron Lett. 2006, 47, 99-103.
141. Lee, S.; MacMillan, D. W. C. Tetrahedron 2006, 62, 11413-11424.
142. Wang, X.; List, B. Angew. Chem. Int. Ed. 2008, 47, 1119-1122.
143. Wang, X.; Reisinger, C. M.; List, B. J. Am. Chem. Soc. 2008, 130, 6070-6071.
144. Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem. Soc. 2008, 130, 8134-8135.
145. (a) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.), New York: Wiley-VCH, 2000; pp. 727-756.
146. (b) Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656-5682.
147. (a) Helder, R.; Hummelen, J. C.; Laane, R. W. P.; M. Wiering, J. S.; Wynberg, H. Tetrahedron Lett. 1976, 17, 1831-1834.
148. (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1998, 39, 1599-1602.
149. (c) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566.
150. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999, 1, 1287-1290.
151. Jew, S.-S.; Lee, J.-H.; Jeong, B.-S.; Yoo, M.-S.; Kim, M.-J.; Lee, Y.-J.; Lee, J.; Choi, S.-H.; Lee, K.; Lah M. S.; Park, H.-G. Angew. Chem. Int. Ed. 2005, 44, 1383-1385.
152. Ooi, T.; Ohara, D.; Tamura, M.; Maruoka, K. J. Am. Chem. Soc. 2004, 126, 6844-6845.
153. (a) Pitchen, P.; Dunach, E.; Deshmukh, M. N.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188-8193.
154. (b) Brunel, J.-M.; Diter, P.; Duetsch, M.; Kagan, H. B. J. Org. Chem. 1995, 60, 8086-8088.
155. Di Furia, F.; Modena, G.; Seraglia, R. Synthesis 1984, 325-326.
156. (a) Bolm, C.; Muñiz, K.; Hildebrand, J. P. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 697-710.
157. (b) Kagan, H. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.). New York: Wiley-VCH, 2000; pp. 327-356.
158. (c) Kagan, H. B.; T'Luukas, O. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 479-495.
159. (d) Fernández, I.; Khiar, N. Chem. Rev. 2003, 103, 3651-3705.
160. Colombo, A.; Marturano, G.; Pasini, A. Gazz. Chim. Ital. 1986, 116, 35-40.
161. (a) Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3873-3876.
162. (a) Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 8333-8336.
163. (a) Tanaka, T.; Saito, B.; Katsuki, T. Tetrahedron Lett. 2002, 43, 3259-3262.
164. (b) Saito, B.; Katsuki, T. Chirality 2003, 15, 24-27.
165. Bolm, C.; Bienewald, F. Angew. Chem. Int. Ed. 1995, 34, 2640-2642.
166. Vetter, A. H.; Berkessel, A. Tetrahedron Lett. 1998, 39, 1741-1744.
167. Ohta, C.; Shimizu, H.; Kondo, A.; Katsuki, T. Synlett 2002, 161-163.
168. Pelotier, B.; Anson, M. S.; Campbell, I. B.; Macdonald, S. J. F.; Priem, G.; Jackson, R. F. W. Synlett 2002, 1055-1060.
169. Drago, C.; Caggiano, L.; Jackson, R. F. W. Angew. Chem. Int. Ed. 2005, 44, 7221-7223.
170. (a) Komatsu, N.; Hashizume, M.; Sugita, T.; Uemura, S. J. Org. Chem. 1993, 58, 7624-7626.
171. (b) Thakur, V. V.; Sudalai, A. Tetrahedron: Asymmetry 2003, 14, 407-410.
172. (c) Jia, X.; Li, X.; Xu, L.; Li, Y.; Shi, Q.; Au-Yeung, T. T.-L.; Yip, C. W.; Yao, X.; Chan, A. S. C. Adv. Synth. Catal. 2004, 346, 723-726.
173. Sun, J.; Zhu, C.; Dai, Z.; Yang, M.; Pan, Y.; Hu, H. J. Org. Chem. 2004, 69, 8500-8503.
174. Miyazaki, T.; Katsuki, T. Synlett 2003, 1046-1048.
175. Legros, J.; Bolm, C. Angew. Chem. Int. Ed. 2003, 42, 5487-5489.
176. White, M. C.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 7194-7195.
177. (a) Legros, J.; Bolm, C. Angew. Chem. Int. Ed. 2004, 43, 4225-4228.
178. (b) Legros, J.; Bolm, C. Chem. Eur. J. 2005, 11, 1086-1092.
179. (a) Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2007, 129, 8940-8941.
180. (b) Egami, H.; Katsuki, T. Synlett 2008, 1543-1546.
181. Scarso, A.; Strukul, G. Adv. Synth. Catal. 2005, 347, 1227-1234.
182. Yamaguchi, T.; Matsumoto, K.; Saito, B.; Katsuki, T. Angew. Chem. Int. Ed. 2007, 46, 4729-4731.
183. (a) Matsumoto, K.; Yamaguchi, T.; Fujisaki, J.; Saito, B.; Katsuki, T. Chem. Asian J. 2008, 3, 351-358.
184. (b) Matsumoto, K.; Yamaguchi, T.; Katsuki, T. Heterocycles 2009, 76, 191-196.
185. Matsumoto, K.; Yamaguchi, T.; Katsuki, T. Chem. Commun. 2008, 1704-1706.
186. Baeyer, A.; Villiger, V. Ber. Dtsch. Chem. Ges. 1899, 32, 3625-3633.
187. (a) Bolm, C.; Beckmann, O. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer, 1999; pp. 803-810.
188. (b) Bolm, C. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 267-274.
189. (c) Bolm, C. In Asymmetric Synthesis-The Essentials (Eds. Christmann, M.; Bräse, S.). Weinheim: Wiley-VCH, 2007; pp. 57-61.
190. (d) ten Brink, G.-J.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Rev. 2004, 104, 4105-4123.
191. (a) Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451.
192. (b) Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Cat. A 1997, 117, 413-423.
193. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. Int. Ed. Engl. 1994, 33, 1848-1849.
194. (a) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett. 1992, 2231-2234.
195. (b) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327-330.
196. Bolm, C.; Beckmann, O.; Palazzi, C. Can. J. Chem. 2001, 79, 1593-1597.
197. (a) Vedejs, E.; Chen, X. J. Am. Chem. Soc. 1997, 119, 2584-2585.
198. (b) Dehli, J. R.; Gotor, V. Chem. Soc. Rev. 2002, 31, 365-370.
199. Frison, J.-C.; Palazzi, C.; Bolm, C. Tetrahedron 2006, 62, 6700-6706.
200. (a) Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 6911-6914.
201. (b) Uchida, T.; Katsuki, T.; Ito, K.; Akashi, S.; Ishii, A.; Kuroda, T. Helv. Chem. Acta 2002, 85, 3078-3089.
202. Aoki, M.; Seebach, D. Helv. Chim. Acta 2001, 84, 187-207.
203. (a) Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481-4485.
204. (b) Watanabe, A.; Uchida, T.; Irie, R.; Katsuki, T. Proc. Natl. Acad. Sci. USA 2004, 101, 5737-5742.
205. Matsumoto, K.; Watanabe, A.; Uchida, T.; Ogi, K.; Katsuki, T. Tetrahedron Lett. 2004, 45, 2385-2388.
206. Ito, K.; Ishii, A.; Kuroda, T.; Katsuki, T. Synlett 2003, 643-646.
207. Malkov, A. V.; Friscourt, F.; Bell, M.; Swarbrick, M. E.; Kocovský, P. J. Org. Chem. 2008, 73, 3996-4003.
208. Berezina, N.; Alphand, V.; Furstoss, R. Tetrahedron: Asymmetry 2002, 13, 1953-1955.
209. Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem. Int. Ed. 2002, 41, 2366-2368.
210. (a) Murahashi, S.-I. Angew. Chem. Int. Ed. Engl. 1995, 34, 2443-2465.
211. (b) Shinkai, S.; Yamaguchi, T.; Manabe, O.; Toda, F. J. Chem. Soc., Chem. Commun. 1988, 1399-1401.
212. Xu, S.; Wang, Z.; Zhang, X.; Zhang, X.; Ding, K. Angew. Chem. Int. Ed. 2008, 47, 2840-2843.
213. Peris, G.; Miller, S. J. Org. Lett. 2008, 10, 3049-3052.
214. (a) Markó, I. E.; Svendsen, J. S. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 713-787.
215. (b) Johnson, R. A.; Sharpless, K. B. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.). New York: Wiley-VCH, 2000; pp. 357-398.
216. (c) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 275-298.
217. (d) Muñiz, K. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 298-307.
218. (a) Bolm, C.; Hildebrand, J. P.; Muñiz, K. In Catalytic Asymmetric Synthesis, 2nd ed. (Ed. Ojima, I.). New York: Wiley-VCH, 2000; pp. 399-428.
219. (b) Kolb, H. C.; Sharpless, K. B. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 309-326.
220. (c) Muñiz, K. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley- VCH, 2004, pp. 326-336.
221. (a) Rubin, A. E.; Sharpless, K. B. Angew. Chem. Int. Ed. 1997, 36, 2637-2640.
222. (b) Pringle, W.; Sharpless, K. B. Tetrahedron Lett. 1999, 40, 5151-5154.
223. (c) Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2001, 40, 3455-3457.
224. (a) Andersson, M. A.; Epple, R.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 472-475.
225. (b) Wu, P.; Hilgraf, R.; Fokin, V. V. Adv. Synth. Catal. 2006, 348, 1079-1085.
226. (a) Döbler, C.; Mehltretter, G. M.; Beller, M. Angew. Chem. Int. Ed. 1999, 38, 3026-3028.
227. (b) Döbler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2000, 122, 10289-10297.
228. (a) Bergstad, K.; Jonsson, S. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 10424-10425.
229. (b) Jonsson, S. Y.; Färnegårdh, K.; Bäckvall, J.-E. J. Am. Chem. Soc. 2001, 123, 1365-1371.
230. Suzuki, K.; Oldenburg, P. D.; Que, L., Jr. Angew. Chem. Int. Ed. 2008, 47, 1887-1889.
231. Chen, M. S.; White, M. C. Science 2007, 318, 783-787.
232. (a) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis, Vol. II (Eds. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H.). Berlin: Springer-Verlag, 1999; pp. 609-618.
233. (b) Mößner, C.; Bolm, C. In Transition Metals for Organic Synthesis, Vol. 2, 2nd ed. (Eds. Beller, M.; Bolm, C.). Weinheim: Wiley-VCH, 2004; pp. 389-402.
234. (c) Müller, P.; Fruit, C. Chem. Rev. 2003, 103, 2905-2919.
235. Evans, D. A.; Faul, M. M.; Bilodeau, M. T.; Anderson, B. A.; Barnes, D. M. J. Am. Chem. Soc. 1993, 115, 5328-5329.
236. Li, Z.; Conser, K. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1993, 115, 5326-5327.
237. Lai, T.-S.; Kwong, H.-L.; Che, C.-M.; Peng, S.-M. Chem. Commun. 1997, 2373-2374.
238. Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245-9248.
239. Cenini, S.; La Monica, G. Inorg. Cheim. Acta. 1976, 18, 279-293.
240. Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889-5890.
241. Mueller, P.; Baud, C.; Naegeli, I. J. Phys. Org. Chem. 1998, 11, 597-601.
242. (a) Omura, K.; Murakami, M.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 354-355.
243. (b) Omura, K.; Uchida, T.; Irie, R.; Katsuki, T. Chem. Commun. 2004, 2060-2061.
244. Katsuki, T. Chem. Lett. 2005, 34, 1304-1309.
245. (a) Kawabata, H.; Omura, K.; Katsuki, T. Tetrahedron Lett. 2006, 47, 1571-1574.
246. (b) Kawabata, H.; Omura, K.; Uchida, T.; Katsuki, T. Chem. Asian J. 2007, 2, 254-256.
247. Nishimura, M.; Minakata, S.; Takahashi, T.; Oderaotoshi, Y.; Komatsu, M. J. Org. Chem. 2002, 67, 2101-2110.
248. Xu, J.; P. Jiao, J. Chem. Soc., Perkin Trans. 1, 2002, 1491-1493.
249. Shen, Y.-M.; Zhao, M.-X.; Xu, J.; Shi, Y. Angew. Chem. Int. Ed. 2006, 45, 8005-8008.
250. Armstrong, A.; Baxter, C. A.; Lamont, S. G.; Page, A. R.; Wincewicz, R. Org. Lett. 2007, 9, 351-353.
251. Vesely, J.; Ibrahem, I.; Zhao, G.-L.; Rios, R.; Córdova, A. Angew. Chem. Int. Ed. 2007, 46, 778-781.