Ryota Nakamura et al.
FULL PAPERS
Tech Research Center” Project for Private Universities:
matching fund subsidy from the Ministry of Education, Cul-
ture, Sports, Science and Technology, 2005–2009, and Re-
search Association for Ishii Oxidation Technology.
[12] a) J. W. J. F. Thuring, G. H. L. Nefkens, M. A. Wegman,
A. J. H. Klunder, B. J. Zwanenburg, J. Org. Chem.
1996, 61, 6931; b) W. H. Miles, D. G. Duca, B. R. Self-
ridge, C. A. Palha De Sousa, K. B. Hamman, E. O.
Goodzeit, J. T. Freedman, Tetrahedron Lett. 2007, 48,
7809.
[13] P. Camps, S. Gimꢄnez, X. Farrꢄs, D. Mauleꢂn, G. Car-
ganico, Liebigs Ann. Chem. 1993, 641.
References
[14] a) R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal.
2004, 346, 1051; b) F. Recupero, C. Punta, Chem. Rev.
2007, 107, 3800.
[15] W. J. de Klein, in: Organic Synthesis by Oxidation with
Metal Compounds, (Ed.: W. J. Mijs, C. R. H. I. de
Jonge), Plenum, New York, 1986, p 261; both the
methyl and acetyl groups of 1a are simultaneously oxi-
dized.
[1] a) V. Calꢂ, P. Giannoccaro, A. Nacci, A. Monopoli, J.
Organomet. Chem. 2002, 645, 152; b) C. M. Kormos,
N. E. Leadbeater, Synlett 2006, 11, 1663; c) P. Berger,
A. Bessmernykh, J.-C. Caille, S. Mignonac, Synthesis
2006, 18, 3106; d) S. Cacchi, C. L. Cotet, G. Fabrizi, G.
Forte, A. Goggiamani, L. Martꢃn, S. Martꢃnez, E.
Molins, M. Moreno-Man¼s, F. Petrucci, A. Roig, A.
Vallriberad, Tetrahedron 2007, 63, 2519.
[16] a) T. Iwahama, S. Sakaguchi, Y. Ishii, Chem. Commun.
2000, 2317; b) K. Hirase, T. Iwahama, S. Sakaguchi, Y.
Ishii, J. Org. Chem. 2002, 67, 970.
[2] V. P. Boyarskii, T. E. Zhesko, E. V. Larionov, V. A. Po-
lukeev, Russ. J. Appl. Chem. 2007, 80, 571.
[3] S. Cacchi, G. Fabrizi, A. Goggiamani, Org. Lett. 2003,
5, 4269.
[4] G. Lesma, A. Sacchetti, A. Silvani, Synthesis 2006, 4,
594.
[17] a) 2a: R. J. Balahura, A. Sorokin, J. Bernadou, B. Meu-
ˇ
nier, Inorg. Chem. 1997, 36, 3488; b) 2b: A. Zabjek, A.
[12b]
ˇ
Petric, Tetrahedron Lett. 1999, 40, 6077; c) 2c: ref.
;
d) 2d: D. Seyferth, M. O. Nestle, A. T. Wehman, J. Am.
Chem. Soc. 1975, 97, 7417; e) 3a: N. Jiang, A. J. Ra-
gauskas, J. Org. Chem. 2007, 72, 7030; f) 3b: H.-R.
Bjørsvik, L. Liguori, J. A. V. Merinero, J. Org. Chem.
2002, 67, 7493; g) 3c: K. Ukai, M. Aoki, J. Takaya, N.
Iwasawa, J. Am. Chem. Soc. 2006, 128, 8706; h) 3d: K.
Nemoto, H. Yoshida, Y. Suzuki, N. Morohashi, T. Hat-
tori, Chem. Lett. 2006, 35, 820; i) 3e: M. D. Otero, B.
Batanero, F. Barba, Tetrahedron Lett. 2006, 47, 8215;
j) 3f: R. Raja, J. M. Thomas, M. Greenhill-Hooperc, V.
Doukova, Chem. Commun. 2007, 1924; k) 3g: B. C.
Ranu, S. Bhadra, L. Adak, Tetrahedron Lett. 2008, 49,
2588; l) 3h: ref.[14k]; m) 3i: ref.[14g]; n) 3j: ref.[14k]; o) 3k:
K. Lee, Y.-H. Kim, S. B. Han, H. Kang, S. Park, W. S.
Seo, J. T. Park, B. Kim, S. Chang, J. Am. Chem. Soc.
2003, 125, 6844; p) 3l: ref.[14h]; q) 3m: ref.[14g]; r) 3o: I.
Hirose, A. Namatame, T. Amamiya, Japanese Patent
JP 61236747, 1986; s) 4a: J. T. Spletstoser, J. M. White,
A. R. Tunoori, G. I. Georg, J. Am. Chem. Soc. 2007,
129, 3408; t) 4b: C. Crisostomo, M. G. Crestani, J. J.
Garcia, J. Mol. Catal. A: Chem. 2007, 266, 139; u) 4c: S.
Mannam, G. Sekar, Tetrahedron Lett. 2008, 49, 2457;
v) 5: J. Mo, J. Xiao, Angew. Chem. 2006, 118, 4258;
Angew. Chem. Int. Ed. 2006, 45, 4152.
[5] E. D. Bergmann, J. A. Blum, J. Org. Chem. 1959, 24,
549.
[6] M. Waser, W. G. Jary, P. Pçchlauer, H. Falk, J. Mol.
Catal. A: Chem. 2005, 236, 187.
[7] F. Minisci, F. Recupero, F. Fontana, H.-R. Bjørsvik, L.
Liguori, Synlett 2002, 4, 610.
[8] a) G. W. Parshall, S. D. Ittel, Homogeneous Catalysis,
2nd edn., Wiley, New York, 1992, p 225; b) C. J. Park,
R. Sheehan, in: Kirk-Othmer Encyclopedia of Chemical
Technology, 4th edn., (Eds.: J. I. Kroschwite, M. Howe-
Grant), John Wiley and Sons, New York, 1996, Vol. 18,
p 991; c) J. R. Sheehan, in: Ullmannꢀs Encyclopedia In-
dustrial Organic Chemicals, (Ed.: F. Ullmann), Wiley-
VCH, Weinheim, Germany, 1999, Vol. 8, p 4575; d) W.
Partenheimer, Catal. Today 1995, 23, 69.
[9] L. G. Bray, J. F. J. Dippy, S. R. C. Hughes, J. Chem. Soc.
1957, 265, and reference cited therein.
[10] a) Y. Ishii, S. Sakaguchi, T. Iwahama, Adv. Synth. Catal.
2001, 343, 393; b) N. Hirai, Y. Tatsukawa, M. Kameda,
S. Sakaguchi, Y. Ishii, Tetrahedron 2006, 62, 6695.
[11] a) Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T.
Iwahama, Y. Nishiyama, J. Org. Chem. 1995, 60, 3934;
b) R. Nakamura, Y. Obora, Y. Ishii, Chem. Commun.
2008, 29, 3417.
1684
ꢀ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2009, 351, 1677 – 1684