Abstract
The recent development of asymmetric Baeyer—Villiger oxidation of prochiral and racemic ketones is briefly summarized, focusing on the regio- and stereocontrol of the oxidation attained by regulating the stereoelectronic demand in the step of rearrangement of the Criegee intermediate.
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References
G. R. Krow, Org. React., 1993, 43, 251.
R. Criege, J. Liebigs Ann. Chem., 1948, 560, 127.
V. Alphand and R. Furstoss, in Handbook of Enzyme Catalysis in Organic Synthesis, Eds K. Drauz, and H. Waldmann, VCH Publishers, Weinheim, 1995, p. 744; (b) S. M. Roberts and P. W. H. Wan, J. Mol. Cat. B: Enzymatic, 1998, 4, 111–136; (c) D. R. Kelly, Chemica Oggi/Chemical Today, 2000, 18, 33, 52.
V. Alphand, A. Archelus, and R. Furstoss, Tetrahedron Lett., 1989, 30, 3663.
F. Bertozzi, P. Crotti, F. Macchia, M. Pineshi, and B. L. Feringa, Angew. Chem., Int. Ed. Engl., 2001, 40, 930.
S.-I. Murahashi, S. Ono, and Y. Imada, Angew. Chem., Int. Ed., 2002, 41, 2366.
C. Bolm, G. Schlingloff, and K. Weickhard, Angew. Chem., Int. Ed., 1994, 33, 1848.
A. Gusso, C. Baccin, F. Pinna, and G. Strukul, Organometallics, 1994, 13, 3442.
C. Bolm and G. Schlingloff, J. Chem. Soc., Chem. Commun., 1995, 1247.
M. Lopp, A. Paju, T. Kanger, and T. Pehk, Tetrahedron Lett., 1996, 37, 7583; (b) C. Bolm, G. G. Schlingloff, and F. Bienewald, J. Mol. Cat. A; Chem., 117, 347; (c) C. Bolm, K. K. Luong, and G. Schlingloff, Synlett., 1997, 1151; (d) C. Bolm and O. Beckmann, Chirality, 2000, 12, 523; (e) T. Shinohara, F. Fujioka, and H. Kotsuki, Heterocycles, 2001, 55, 237.
C. Bolm, O. Beckmann, A. Cosp, and C. Palazzi, Synlett., 2001, 1461.
C. Bolm, O. Beckmann, and C. Palazzi, Can. J. Chem., 2001, 79, 1593.
M. Aoki and D. Seebach, Helv. Chim. Acta, 2001, 84, 187.
T. Uchida and T. Katsuki, Tetrahedron Lett., 2001, 42, 6911.
M.-C. Cheng, M. C.-W. Chang, S.-M. Peng, K.-K. Cheung, and C.-M. Che, J. Chem. Soc., Dalton Trans., 1997, 3479.
A. Gusso, C. Baccin, F. L. Pinna, and G. Strukul, Organometallics, 1999, 18, 5067.
M. M. Ali, Rev. Inorg. Chem., 1996, 16, 315.
Y. Belokon’, S. Caveda-Cepas, B. Green, N. Ikonnikov, V. Khrustalev, V. Larichev, M. Moskalenko, M. North, C. Orizu, V. Tararov, M. Tasinazzo, G. Timofeeva, and L. Yashkina, J. Am. Chem. Soc., 1999, 121, 3968; (b) Y. Belokon’, B. Green, N. Ikonnikov, V. Khrustalev, V. Larichev, B. Lokshin, M. Moskalenko, M. North, C. Orizu, A. Peregudov, and G. Timofeeva, Eur. J. Org. Chem., 2000, 2655.
B. Saito and T. Katsuki, Tetrahedron Lett., 2001, 42, 3873; b) B. Saito and T. Katsuki, Tetrahedron Lett., 2001, 42, 8333.
A. Watanabe, T. Uchida, K. Ito, and T. Katsuki, Tetrahedron Lett., 2002, 43, 4481.
G. Helmchen and S. Roland, Angew. Chem., Int. Ed. (Engl.), 1981, 93, 208.
A. Watanabe, T. Uchida, R. Irie, and T. Katsuki, Proc. of the National Academy of Sciences (PNAS), 2004, 101, 5737.
F. Corazza, E. Solari, C. Floriani, A. Chiesi-Villa, and C. Guastini, J. Chem. Soc., Dalton Trans., 1990, 1335.
K. Ito, A. Ishii, T. Kuroda, and T. Katsuki, Synlett., 2003, 643.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1784–1794, September, 2004.
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Katsuki, T. Asymmetric Baeyer—Villiger oxidation: control of stereoelectronic demand. Russ Chem Bull 53, 1859–1870 (2004). https://doi.org/10.1007/s11172-005-0044-7
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DOI: https://doi.org/10.1007/s11172-005-0044-7