Abstract
Molecular oxygen is often expected to be the easily available oxidant, but its utilization in organic synthesis has been restricted to several reactions because of the difficulties in carrying a desired reaction out exclusively. Molecular oxygen is caputured and activated by transition-metal complexes coordinated by organic ligands whose stereochmical and electrochemical properties could be tuned by modofication of its ligand systems. Several new and efficient synthetic oxidation reactions of olefins using molecular oxygen were recently developed based on the above concept.
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References
I. Tabushi and N. Koga, J. Am. Chem. Soc. ,101, 6456 (1979)
I. Tabushi and A. Yamazaki, ibid. ,103, 2884 (1983).
T. Okamoto and S. Oka, J. Org. Chem. ,49, 1589 (1984).
S. Inoue, Y. Ohkatsu, M. Ohno, and T. Ooi, Nippon Kgaku Kaishi ,1985, 387.
A. Zombeck, D. E. Hamilton, and R. S. Drago, J. Am. Chem. Soc. ,104, 6782 (1982)
D. E. Hamilton, R. S.Drago, and A. Zombeck, ibid. ,109, 374 (1987)
A. Nishinaga, H. Yamato, T. Abe, K. Maruyama, and T. Matsuura, Tetrahedron Lett. ,29, 6309 (1988).
E. P. Talsi, Y. S. Zimin, and V. M. Nekipelov, React. Kinet. Catal. Lett. ,27, 361 (1985).
T. Mukaiyama, S. Isayama, S. Inoki, K. Kato, T. Yamada, and T. Takai, Chem. Lett. ,1989, 449.
S. Inoki, K. Kato, T. Takai, S. Isayama, T. Yamada, and T. Mukaiyama, Chem. Lett. ,1989, 515.
K. Kato, T. Yamada, T. Takai, S. Inoki, and S. Isayama, Bull. Chem. Soc. Jpn. ,63, 179 (1990).
T. Yamada and T. Mukaiyama, Chem. Lett. ,1989, 519.
K. Kato and T. Mukaiyama, Chem. Lett. ,1989, 2233.
S. Inoki and T. Mukaiyama, Chem. Lett. ,1990, 67.
J. D. Citron, J. Org. Chem. ,36, 2547 (1971).
S. Isayama and T. Mukaiyama, Chem. Lett. ,1989, 569.
S. Isayama and T. Mukaiyama, Chem. Lett. ,1989, 573.
S. Isayama, Bull. Chem. Soc. Jpn. ,63, 1305 (1990).
S. Isayama and T. Mukaiyama, Chem. Lett. ,1989, 1071.
S. Inoki, K. Kato, S. Isayama, and T. Mukaiyama, Chem. Lett. ,1990, 1869.
S. Isayama and T. Mukaiyama, Chem. Lett. ,1989, 2005.
M. Tavarès, R. Ramasseul, J.-C. Marchon, B. Bachet, C. Brassy, and J.-P. Mornon, J. Chem. Soc., Perkin Trans. 2 ,1992, 1321.
Y. Matsuda, H. Koshima, K. Nakamura, and Y. Murakami, Chem. Lett. ,1988, 625.
T. Takai, T. Yamada, and T. Mukaiyama, Chem. Lett. ,1990, 1657.
T. Mukaiyama, T. Takai, T. Yamada, and O. Rhode, Chem. Lett. ,1990, 1661.
T. Yamada, T. Takai, O. Rhode, and T. Mukaiyama, Chem. Lett. ,1991, 1.
Nippon Soda Co., Ltd., JP Patent Tokkaisho 46-26063 (1971).
Y. Maeda, M. Ai, and S. Suzuki, Kogyo Kagaku Zasshi ,73, 99 (1970).
Shell International Research, JP Patent Tokkaisho 59-231077 (1984).
T. Yamada, T. Takai, O. Rhode, and T. Mukaiyama, Bull. Chem. Soc. Jpn. ,64, 2109 (1991).
T. Takai, T. Yamada, O. Rhode, and T. Mukaiyama, Chem. Lett. ,1991, 281.
T. Takai, E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Jpn. ,64, 2513 (1991).
S. Inoki, T. Takai, T. Yamada, and T. Mukaiyama, Chem. Lett. ,1991, 941.
T. Takai, T. Yamada, and T. Mukaiyama, Chem. Lett. ,1991, 1499.
T. Mukaiyama, K. Imagawa, T. Yamada, and T. Takai, Chem. Lett. ,1992, 231.
T. Yamada, O. Rhode, T. Takai, and T. Mukaiyama, Chem. Lett. ,1991, 5.
T. Yamada, K. Takahashi, K. Kato, T. Takai, S. Inoki, and T. Mukaiyama, Chem. Lett. ,1991, 641.
B. E. Rossiter, “Synthetic Aspects and Applications of Asymmetric Epoxidation”,1991 in “Asymmetric Synthesis”,1991 ed by J. D. Morrison, Academic Press, Inc., New York (1985), Vol.5, Chap.7, pp.194.
H. Nohira, S. Nakamura, and M. Kamei, Mol. Cryst. Liq. Cryst. ,180B, 379 (1990).
T. Katsuki and K. B. Sharpless, J. Am. Chem. Soc. ,102, 5974 (1980).
S. W. May and R. D. Schwartz, J. Am. Chem. Soc. ,96, 4031 (1974)
H. Ohta and H. Tetsukawa, J. Chem. Soc., Chem. Commun. ,1978, 849
K. Furuhashi and M. Takagi, Appl. Microbiol. Biotechnol. ,20, 6 (1984).
J. T. Groves and R. S. Myers, J. Am. Chem. Soc. ,105, 5791 (1983)
Y. Naruta, F. Tani, N. Ishihara, and K.Maruyama, ibid. ,113, 6865 (1991).
W.Zhang, J. L. Loebach, S. R. Wilson, and E. N. Jacobsen, J. Am. Chem. Soc. ,112, 2801 (1990).
R. Irie, K. Noda, Y. Ito, N. Matsumoto, and T. Katsuki, Tetrahedron Lett. ,31, 7345 (1990).
W. Zhang and E. N. Jacobsen, J. Org. Chem. ,56, 2296 (1991).
Y. Kaku, M. Otsuka, and M. Ohno, Chem. Lett. ,1989, 611.
T. Yamada, K. Imagawa, and T. Mukaiyama, Chem. Lett. ,1992, 2109.
P. Brougham, M. S. Cooper, D. A. Cummerson, H. Heaney, and N. Thompson, Synthesis ,1987, 1015.
J.-C. Marchon and R. Ramasseul, Synthesis ,1989, 389.
T. Yamada, K. Imagawa, T. Nagata, and T. Mukaiyama, Chem. Lett. ,1992, 2231.
T. Mukaiyama, T. Yamada, T. Nagata, and K. Imagawa, Chem. Lett. ,1993, 327.
T. Takai, E. Hata, K. Yorozu, and T. Mukaiyama, Chem. Lett. ,1992, 2077.
T. Mukaiyama, K. Yorozu, T. Takai, and T. Yamada, Chem. Lett. ,1993, 439.
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Mukaiyama, T. (1993). Oxygenation of Olefins with Molecular Oxygen Catalyzed by Low Valent Metal Complexes. In: Barton, D.H.R., Martell, A.E., Sawyer, D.T. (eds) The Activation of Dioxygen and Homogeneous Catalytic Oxidation. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3000-8_11
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DOI: https://doi.org/10.1007/978-1-4615-3000-8_11
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