Some recent advances in metallosalen chemistry

Synlett

Volumn , Issue 3, 2003, Pages 281-297

  Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Cyclopropanation; Epoxidation; Metallosalen complex; Molecular oxygen

Indexed keywords

ALKENE DERIVATIVE; COBALT; HYDROGEN PEROXIDE; MANGANESE; METAL COMPLEX; OXYGEN; RUTHENIUM; TITANIUM;

ARTICLE; CATALYST; CHEMISTRY; CHIRALITY; ENANTIOSELECTIVITY; MOLECULAR BIOLOGY; OXIDATION; X RAY ANALYSIS;

EID: 0037288744     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-37101     Document Type: Article

References (181)

1. Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons Inc.: New York, 1994.
2. Aratani, T. In Comprehensive Asymmetric Catalysis, Vol. III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 2000, 1451-1460.
3. (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; John Wiley & Sons: New York, 1998.
4. (b) Davies, H. M. L. Curr. Org. Chem. 1998, 2, 463.
5. (a) Katsuki, T. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; Wiley-VCH: New York, 2000, 2nd Ed., 287-325.
6. (b) Jacobsen, E. N. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 2000, 649-677.
7. Evans, D. A. In Asymmetric Oxidation Reactions, Practical Approach in Chemistry; Katsuki, T., Ed.; Oxford University Press: Oxford, 2001, 115-128.
8. Samsel, E. G.; Srinivasan, K.; Kochi, J. K. J. Am. Chem. Soc. 1985, 107, 7606.
9. Srinivasan, K.; Michaud, P.; Kochi, J. K. J. Am. Chem. Soc. 1986, 108, 2309.
10. (a) Feichtinger, D.; Plattner, D. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 1718.
11. (b) Feichtinger, D.; Plattner, D. A. Chem.-Eur. J. 2001, 7, 591.
12. Zhang, W.; Loebach, J. L.; Wilson, S. R.; Jacobsen, E. N. J. Am. Chem. Soc. 1990, 112, 2801.
13. Irie, R.; Noda, K.; Ito, Y.; Matsumoto, N.; Katsuki, T. Tetrahedron Lett. 1990, 31, 7345.
14. (a) Katsuki, T. J. Mol. Chem. A: Chem. 1996, 113, 87.
15. (b) Katsuki, T. Coord. Chem. Rev. 1995, 140, 189.
16. (c) Jacobsen, E. N. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Inc.: New York, 1993, 159-202.
17. (a) Yamashita, Y.; Katsuki, T. Synlett 1995, 829.
18. (b) Noguchi, Y.; Irie, R.; Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4533.
19. (a) Hashihayata, T.; Ito, Y.; Katsuki, T. Synlett 1996, 1079.
20. (b) Hashihayata, T. Ito, Y. Katsuki, T. Tetrahedron 1997, 53, 9541.
21. (c) Miura, K.; Katsuki, T. Synlett 1999, 783.
22. Hamada, T.; Irie, R.; Katsuki, T. Synlett 1994, 479.
23. (a) Sasaki, H.; Irie, R.; Hamada, T.; Suzuki, K.; Katsuki, T. Tetrahedron 1994, 50, 11827.
24. (b) Fukuda, T.; Irie, R.; Katsuki, T. Synlett 1995, 197.
25. (a) Punniyamurthy, T.; Irie, R.; Katsuki, T.; Akita, M.; Moro-oka, Y. Synlett 1999, 1049.
26. (b) Hashihayata, T.; Punniyamurthy, T.; Irie, R.; Katsuki, T.; Akita, M.; Moro-oka, Y. Tetrahedron 1999, 55, 14599.
27. For a preliminary review of second-generation Mn(salen)-catalyzed reactions, see: Ito, Y. N.; Katsuki, T. Bull. Chem. Soc. Jpn. 1999, 72, 603.
28. (a) Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1995, 36, 7739.
29. (b) Ryan, K. M.; Bousquet, C.; Gilheany, D. G. Tetrahedron Lett. 1999, 40, 3613.
30. (c) O'Mahony, C. P.; McGarrigle, E. M.; Renehan, M. F.; Ryan, K. M.; Kerrigan, N. J.; Bousquet, C.; Gilheany, D. G. Org. Lett. 2001, 3, 3435.
31. Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 649-693.
32. (a) Nishikori, H.; Ohta, C.; Oberlin, E.; Irie, R.; Katsuki, T. Tetrahedron 1999, 55, 13937.
33. (b) Ohta, C.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3885-3888.
34. Nishikori, H.; Ohta, C.; Katsuki, T. Synlett 2000, 1557.
35. (a) Reddeppa Reddy, D.; Thornton, E. R. J. Chem. Soc., Chem. Commun. 1992, 172.
36. (b) Chang, S.; Heid, R. M.; Jacobsen, E. N. Tetrahedron Lett. 1994, 35, 669.
37. (c) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Möller, C. R. J. Am. Chem. Soc. 1998, 120, 708-714.
38. Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4389.
39. Palucki, M.; Pospicil, P. J.; Zhang, W.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333.
40. (a) Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R. J. Mol. Cat. A: Chem. 1995, 96, 117.
41. (b) Kureshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Cat. A: Chem. 1995, 96, 33.
42. (a) Gross, Z.; Ini, S.; Kapon, M.; Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
43. (b) Berkessel, A.; Fraenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 3365.
44. (c) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583.
45. (d) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 409.
46. (e) Gross, Z.; Ini, S. Org. Lett. 1999, 1, 2077.
47. (a) End, N.; Pfaltz, A. Chem. Commun. 1998, 589.
48. (b) End, N.; Macko, L.; Zehnder, M.; Pfaltz, A. Chem.-Eur. J. 1998, 4, 818.
49. (a) Fung, W.-H.; Cheng, W.-C.; Yu, W.-Y.; Che, C.-M.; Mak, T. C. W. J. Chem. Soc., Chem. Commun. 1995, 2007.
50. (b) Nishiyama, H.; Shimada, T.; Itoh, H.; Sugiyama, H.; Motoyama, Y. Chem. Commun. 1997, 1863.
51. (a) Takeda, T.; Irie, R.; Shinoda, Y.; Katsuki, T. Synlett 1999, 1157.
52. (b) Nakata, K.; Takeda, T.; Mihara, J.; Hamada, T.; Irie, R.; Katsuki, T. Chem.-Eur. J. 2001, 7, 3776.
53. (c) Mihara, J.; Hamada, T.; Takeda, T.; Irie, R.; Katsuki, T. Synlett 1999, 1160.
54. Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545.
55. Takeda, T.; Irie, R.; Katsuki, T. Synlett 1999, 1166.
56. Velde, S. L. V.; Jacobsen, E. N. J. Org. Chem. 1995, 60, 5380.
57. Noguchi, Y.; Irie, R.; Fukuda, T.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4533.
58. Noguchi, Y.; Takiyama, H.; Katsuki, T. Synlett 1998, 543.
59. Kaufman, M. D.; Grieco, P. A.; Bougie, D. W. J. Am. Chem. Soc. 1993, 115, 11648.
60. Larrow, J. F.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 12129.
61. Hamachi, K.; Irie, R.; Katsuki, T. Tetrahedron Lett. 1996, 37, 4979.
62. Groves, J. T.; Viski, T. J. Org. Chem. 1990, 55, 3628.
63. Hamada, T.; Irie, R.; Mihara, J.; Hamachi, K.; Katsuki, T. Tetrahedron 1998, 54, 1001.
64. (a) Miyafuji, A.; Katsuki, T. Synlett 1997, 836.
65. (b) Miyafuji, A.; Katsuki, T. Tetrahedron 1998, 54, 10339.
66. (c) Miyafuji, A.; Ito, K.; Katsuki, T. Heterocycles 2000, 52, 261.
67. Nishida, T.; Miyafuji, A.; Ito, Y. N.; Katsuki, T. Tetrahedron Lett. 2000, 41, 7053.
68. (a) Punniyamurthy, T.; Miyafuji, A.; Katsuki, T. Tetrahedron Lett. 1998, 39, 8295.
69. (b) Punniyamurthy, T.; Katsuki, T. Tetrahedron 1999, 55, 9439.
70. Komiya, N.; Noji, S.; Murahashi, S.-i. Tetrahedron Lett. 1998, 39, 7921.
71. (a) Kagan, H. B. In Catalytic Asymmetric Synthesis, 2nd Ed.; Ojima, I., Ed.; Wiley-VCH: New York, 2000, Chap 6c.
72. (b) Kagan, H. B. In Asymmetric Oxidation Reactions, Practical Approach in Chemistry; Katsuki, T., Ed.; Oxford University Press: Oxford, 2001, Chap. 4.1.
73. (c) Bolm, C.; Muniz, K.; Hildebrand, J. P. In Comprehensive Asymmetric Catalysis, Vol. II; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 697-710.
74. Nakajima, K.; Kojima, M.; Fujita, J. Chem. Lett. 1986, 1483.
75. Sasaki, C.; Nakajima, K.; Kojima, M.; Fujita, J. Bull. Chem. Soc. Jpn. 1991, 64, 1318.
76. Palucki, M.; Hanson, P.; Jacobsen, E. N. Tetrahedron Lett. 1992, 33, 7111.
77. (a) Kokubo, C.; Katsuki, T. Tetrahedron 1996, 52, 13895.
78. (b) Noda, K.; Hosoya, N.; Irie, R.; Yamashita, Y.; Katsuki, T. Tetrahedron 1994, 50, 9609.
79. (a) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; Larichev, V. S.; Lokshin, B. V.; Moskalenko, M. A.; North, M.; Orizu, C.; Peregudov, A. S.; Timofeeva, G. Eur. J. Org. Chem. 2000, 2655.
80. (b) Belokon, Y. N.; Green, B.; Ikonnikov, N. S.; North, M.; Parsons, T.; Tararov, V. I. Tetrahedron 2001, 57, 771.
81. (a) Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3873.
82. (b) Saito, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 8333.
83. O'Connor, K. J.; Wey, S. J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001.
84. Noda, K.; Hosoya, N.; Irie, R.; Ito, Y.; Katsuki, T. Synlett 1993, 469.
85. Nishikori, H.; Katsuki, T. Tetrahedron Lett. 1996, 37, 9245.
86. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915.
87. Minakata, S.; Ando, T.; Nishimura, M.; Ryu, I.; Komatsu, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3392.
88. (a) Mahy, J. P.; Bedi, G.; Battioni, P.; Mansuy, D. Tetrahedron Lett. 1988, 29, 1927.
89. (b) Evans, D. A.; Faul, M. M.; Bilodeau, M. T. J. Am. Chem. Soc. 1994, 116, 2742.
90. (c) Müller, P.; Baud, C.; Jacquier, Y. Tetrahedron 1996, 52, 1543.
91. (d) Nägeli, I.; Baud, C.; Bernardineli, G.; Jacquier, Y.; Moran, M.; Müler, P. Helv. Chim. Acta 1997, 80, 1087.
92. Kohmura, Y.; Katsuki, T. Tetrahedron Lett. 2001, 42, 3339.
93. Similar phenomena have been observed in metalloporphyrin-catalyzed nitrene-transfer reactions: (a) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531. (b) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233. (c) Yang, J.; Weinberg, R.; Breslow, R. Tetrahedron Lett. 2000, 41, 8063.
94. Similar phenomena have been observed in metalloporphyrin-catalyzed nitrene-transfer reactions: (a) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531. (b) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233. (c) Yang, J.; Weinberg, R.; Breslow, R. Tetrahedron Lett. 2000, 41, 8063.
95. Similar phenomena have been observed in metalloporphyrin-catalyzed nitrene-transfer reactions: (a) Yang, J.; Weinberg, R.; Breslow, R. Chem. Commun. 2000, 531. (b) Yu, X.-Q.; Huang, J.-S.; Zhou, X.-G.; Che, C.-M. Org. Lett. 2000, 2, 2233. (c) Yang, J.; Weinberg, R.; Breslow, R. Tetrahedron Lett. 2000, 41, 8063.
96. For other examples of asymmetric C-H amination, see: (a) Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087. (b) Kohmura, Y.; Kawasaki, K.; Katsuki, T. Synlett 1997, 1456. (c) Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Che, C.-M. Chem. Commun. 1999, 2377.
97. For other examples of asymmetric C-H amination, see: (a) Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087. (b) Kohmura, Y.; Kawasaki, K.; Katsuki, T. Synlett 1997, 1456. (c) Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Che, C.-M. Chem. Commun. 1999, 2377.
98. For other examples of asymmetric C-H amination, see: (a) Nägeli, I.; Baud, C.; Bernardinelli, G.; Jacquier, Y.; Moran, M.; Müller, P. Helv. Chim. Acta 1997, 80, 1087. (b) Kohmura, Y.; Kawasaki, K.; Katsuki, T. Synlett 1997, 1456. (c) Zhou, X.-G.; Yu, X.-Q.; Huang, J.-S.; Che, C.-M. Chem. Commun. 1999, 2377.
99. (a) Cram, D. J.; Day, J.; Rayner, D. R.; von Schriltz, D. M.; Duchamp, D. J.; Garwood, D. C. J. Am. Chem. Soc. 1970, 92, 7369.
100. (b) Annunziata, R.; Cinquini, M.; Colonna, S.; Cozzi, F. J. Chem. Soc., Perkin Trans. 1 1981, 3118.
101. (a) Celentano, G.; Colonna, S.; Gaggero, N.; Richelmi, C. Chem. Commun. 1998, 701.
102. (b) Takada, H.; Ohe, K.; Uemura, S. Angew. Chem. Int. Ed. 1999, 38, 1288.
103. (c) Takada, H.; Oda, M.; Oyamada, A.; Ohe, K.; Uemuram, S. Chirality 2000, 12, 299.
104. (a) Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S. J. Chem. Soc., Chem. Commun. 1996, 931.
105. (b) Takada, H.; Nishibayashi, Y.; Ohe, K.; Uemura, S.; Baird, C. P.; Sporey, T. J.; Taylor, P. C. J. Org. Chem. 1997, 62, 6512.
106. (c) Baird, C. P.; Clark, A. J.; Rooke, S. M.; Sparey, T. J.; Taylor, P. C. Phosphorus, Sulfur Silicon Relat. Elem. 1997, 120-121, 365.
107. (d) Miyake, Y.; Takada, H.; Ohe, K.; Uemura, S. J. Chem. Soc., Perkin Trans. 1 1998, 2373.
108. (a) Li, Z.; Quan, R. W.; Jacobsen, E. N. J. Am. Chem. Soc. 1995, 117, 5889.
109. (b) Bach, T.; Körber, C. Eur. J. Org. Chem. 1999, 1033.
110. Murakami, M.; Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 7071.
111. (a) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 16, 1707.
112. (b) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 18, 2599.
113. (c) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982, 23, 685.
114. Nakamura, A.; Konishi, A.; Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3443.
115. Fukuda, T.; Katsuki, T. Synlett 1995, 825.
116. Fukuda, T.; Katsuki, T. Tetrahedron 1997, 53, 7201.
117. (a) Maxwell, J. L.; O'Malley, S.; Brown, K. C.; Kodadek, T. Organometallics 1992, 11, 645.
118. (b) Doyle, M. P.; Zhou, Q.-L.; Simonsen, S. H.; Lynch, V. Synlett 1996, 697.
119. (c) Ishitani, H.; Achiwa, K. Synlett 1997, 781.
120. (d) Seitz, W. J.; Saha, A. K.; Hossain, M. M. Organometallics 1993, 12, 2604.
121. (e) Doyle, M. P.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867.
122. (a) Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1163.
123. (b) Uchida, T.; Irie, R.; Katsuki, T. Synlett 1999, 1793.
124. (c) Uchida, T. Irie, R. Katsuki, T. Tetrahedron 1996, 56, 3501.
125. (a) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 3647.
126. (b) Niimi, T.; Uchida, T.; Irie, R.; Katsuki, T. Adv. Synth. Catal. 2001, 343, 79.
127. (a) Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521.
128. (b) Saha, B.; Uchida, T.; Katsuki, T. Synlett 2001, 114.
129. (a) Masui, M.; Ando, A.; Shioiri, T. Tetrahedron Lett. 1988, 29, 2835.
130. (b) Dehmlow, E. V.; Knufinke, V. Liebigs Ann. Chem. 1992, 283.
131. (c) Dehmlow, E. V.; Romero, M. J. Chem. Res., Synop. 1992, 400.
132. (d) de Vries, E. F. J.; Ploeg, L.; Colao, M.; Brussee, J.; van der Gen, A. Tetrahedron: Asymmetry 1995, 6, 1123.
133. Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
134. Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583.
135. (a) Yamada, T.; Takai, T.; Rhode, O.; Mukaiyama, T. Chem. Lett. 1991, 1.
136. (b) Inoki, S.; Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1991, 941.
137. (c) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Chem. Lett. 1992, 2231.
138. (d) Mukaiyama, T.; Yamada, T.; Nagata, T.; Imagawa, K. Chem. Lett. 1993, 327.
139. (e) Yamada, T.; Imagawa, K.; Nagata, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1994, 67, 2248.
140. (f) Nagata, T.; Imagawa, K.; Yamada, T.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1995, 68, 1455.
141. (g) For the oxidation using a combination of molecular oxygen and aldehyde, see also: Murahashi, S.-i.; Saito, T.; Naota, T.; Kumobayashi, H.; Akutagawa, S. Tetrahedron Lett. 1991, 32, 5991.
142. (h) See also: Hosokawa, T.; Aoki, S.; Takano, M.; Nakahira, T.; Yoshida, Y.; Murahashi, S.-i. J. Chem. Soc., Chem. Commun. 1991, 1559.
143. (i) See also: Murahashi, S.-i.; Oda, Y.; Naota, T.; Komiya, N. J. Am. Chem. Soc. 1992, 114, 7913.
144. Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848.
145. (a) Nakajima, M.; Kanayama, K.; Miyoshi, I.; Hashimoto, S. Tetrahedron Lett. 1995, 36, 9519.
146. (b) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
147. (a) Hon, S.-W.; Li, C.-H.; Kuo, J.-H.; Barhate, N.-B.; Liu, Y.-H.; Wang, Y.; Chen, C.-T. Org. Lett. 2001, 3, 869.
148. (b) Li, X.; Yang, J.; Kozlowski, M. C. Org. Lett. 2001, 3, 1137.
149. (a) Döbler, C.; Mehltreter, G. M.; Beller, M. Angew. Chem. Int. Ed. 1999, 38, 3026.
150. (b) Döbler, C.; Mehltretter, G. M.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2000, 122, 10289.
151. (c) Krief, A.; Colaux-Castillo, C. Tetrahedron Lett. 1999, 40, 4189.
152. (a) Jensen, D. R.; Pugsley, J. S.; Sigman, M. S. J. Am. Chem. Soc. 2001, 123, 7475.
153. (b) Ferreira, E. M. Stoltz, B. M. J. Am. Chem. Soc. 2001, 123, 7725.
154. Masutani, K.; Uchida, T.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2000, 41, 5119.
155. Masutani, K.; Katsuki, T. unpublished results.
156. Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000, 1433.
157. Cardillo, B.; Cornia, M.; Merlini, L. Gazz. Chim. Ital. 1975, 105, 1151.
158. Masutani, K.; Irie, R.; Katsuki, T. Chem. Lett. 2002, 36.
159. Odenkirk, W.; Rheingold, A. L.; Bosnich, B. J. Am. Chem. Soc. 1992, 114, 6392.
160. Miyata, A.; Murakami, M.; Irie, R.; Katsuki, T. Tetrahedron Lett. 2001, 42, 7067.
161. Alphand, V.; Furstoss, R. In Asymmetric Oxidation Reactions, Practical Approach in Chemistry; Katsuki, T., Ed.; Oxford University Press: Oxford, 2001, Chap. 5.3.
162. Yamada, T.; Takahashi, K.; Kato, K.; Takai, T.; Inoki, S.; Mukaiyama, T. Chem. Lett. 1991, 641.
163. For other Baeyer-Villiger reactions using molecular oxygen, see: (a) Murahashi, S.-i.; Oda, Y.; Naota, T. Tetrahedron Lett. 1992, 33, 7557. (b) Hamamoto, M.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 6421. (c) Bolm, C.; Schlingloff, G.; Weickhardt, K. Tetrahedron Lett. 1993, 34, 3405.
164. For other Baeyer-Villiger reactions using molecular oxygen, see: (a) Murahashi, S.-i.; Oda, Y.; Naota, T. Tetrahedron Lett. 1992, 33, 7557. (b) Hamamoto, M.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 6421. (c) Bolm, C.; Schlingloff, G.; Weickhardt, K. Tetrahedron Lett. 1993, 34, 3405.
165. For other Baeyer-Villiger reactions using molecular oxygen, see: (a) Murahashi, S.-i.; Oda, Y.; Naota, T. Tetrahedron Lett. 1992, 33, 7557. (b) Hamamoto, M.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 6421. (c) Bolm, C.; Schlingloff, G.; Weickhardt, K. Tetrahedron Lett. 1993, 34, 3405.
166. Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442.
167. (a) Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247.
168. (b) Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583.
169. (c) Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Cat. A: Chem. 1997, 117, 347.
170. (d) Strukul, G.; Varagnolo, A.; Pinna, F. J. Mol. Cat. A: Chem. 1997, 117, 413.
171. (e) Kanger, T.; Kriis, K.; Paju, A.; Pehk, T.; Lopp, M. Tetrahedron: Asymmetry 1988, 9, 4475.
172. (f) Bolm, C.; Luong, K. K.; Schlingloff, G. Synlett 1997, 1151.
173. (g) Bolm, C.; Beckmann, O. Chirality 2000, 12, 523.
174. (h) Shinohara, T.; Fujioka, S.; Kotsuki, H. Heterocycles 2001, 55, 237.
175. (a) Bolm, C.; Beckmann, O. In Comprehensive Asymmetric Catalysis, Vol.2; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, 803-810.
176. (b) Strukul, G. Angew. Chem. Int. Ed. 1998, 37, 1198.
177. Good enantioselectivities of 65% and 77% ee's have recently been observed in Baeyer-Villiger reaction of 3-phenylcyclobutanone using chiral magnesium and aluminum complexes,respectively, as the catalysts: (a) Bolm, C.; Beckmann, O.; Cosp, A.; Palazzi, C. Synlett 2001, 1461. (b) Bolm, C.; Beckmann, O.; Palazzi, C. Can. J. Chem. 2001, 79, 1593.
178. Good enantioselectivities of 65% and 77% ee's have recently been observed in Baeyer-Villiger reaction of 3-phenylcyclobutanone using chiral magnesium and aluminum complexes,respectively, as the catalysts: (a) Bolm, C.; Beckmann, O.; Cosp, A.; Palazzi, C. Synlett 2001, 1461. (b) Bolm, C.; Beckmann, O.; Palazzi, C. Can. J. Chem. 2001, 79, 1593.
179. Cheng, M.-C.; Chang, M. C.-W.; Peng, S.-M.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1997, 3479.
180. Uchida, T.; Katsuki, T. Tetrahedron Lett. 2001, 42, 6911.
181. High enantioselectivity of 87% ee has recently been achieved in the Baeyer-Villiger reaction of 3-phenyl-cyclobutanone by using Zr(salen) as the catalyst: Watanabe, A.; Uchida, T.; Ito, K.; Katsuki, T. Tetrahedron Lett. 2002, 43, 4481.