Kazuya Yamaguchi et al.
COMMUNICATIONS
Acknowledgements
[7] Asymmetric cyanosilylations: a) Y. N. Belokon’, S.
Caveda-Cepas, B. Green, N. S. Ikonnikov, V. N. Khrus-
talev, V. S. Larichev, M. A Moscalenko, M. North, C.
Orizu, V. I. Tararov, M. Tasinazzo, G. I. Timofeeva,
L. V. Yashkian, J. Am. Chem. Soc. 1999, 121, 3968;
b) Y. Hamashima, D. Sawada, M. Kanai, M. Shibasaki,
J. Am. Chem. Soc. 1999, 121, 2641; c) I. P. Holmes,
H. B. Kagan, Tetrahedron Lett. 2000, 41, 7453; d) Y.
Hamashima, M. Kanai, M. Shibasaki, J. Am. Chem.
Soc. 2000, 122, 7412; e) F. Chen, X. Feng, B. Qin, G.
Zhang, Y. Jiang, Org. Lett. 2003, 5, 949; f) H. Deng,
M. P. Isler, M. L. Snapper, A. H. Hoveyda, Angew.
Chem. Int. Ed. 2002, 41, 1009; g) Y. Kitani, T. Kuma-
moto, T. Isobe, K. Fukuda, T. Ishikawa, Adv. Synth.
Catal. 2005, 347, 1653.
[8] a) H. Firouzabadi, N. Iranpoor, A. A. Jafari, J. Organo-
met. Chem. 2005, 690, 1556; b) M. L. Kantam, P. Sree-
kanth, P. L. Santhi, Green Chem. 2000, 2, 47; c) Y.
Izumi, M. Onaka, J. Mol. Catal. 1992, 74, 35.
[9] For cyanosilylation ofcyclopentanone as a model reac-
tion, the first-order dependence of the initial rate on
the amount ofcatalyst in the range of50–200 mass%
with respect to cyclopentanone was observed. In addi-
tion, the quantitative yield ofthe corresponding cyano-
hydrin trimethylsilyl ether was obtained with the 50
mass% catalyst (only 0.8 mol% with respect to cyclo-
pentanone) while it required longer reaction time
(20 h).
This work was supported by the Core Research for Evolu-
tional Science and Technology (CREST) program of the
Japan Science and Technology Agency (JST) and the Grants-
in-Aid for Scientific Researches from Ministry of Education,
Culture, Sports, Science and Technology.
References
[1] a) R. A. Sheldon, H. van Bekkum, Fine Chemical
through Heterogeneous Catalysis, Wiley, Weinheim,
2001; b) P. T. Anastas, J. C. Warner, Green Chemistry:
Theory and Practice, Oxford University Press, London,
1998; c) R. A. Sheldon, Green Chem. 2000, 2, G1;
d) P. T. Anastas, L. B. Bartlett, M. M. Kirchhoff, T. C.
Williamson, Catal. Today 2000, 55, 11.
[2] a) P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001,
40, 3727; b) P. I. Dalko, L. Moisan, Angew. Chem. Int.
Ed. 2004, 43, 5138; c) T. Ooi, K. Maruoka, Acc. Chem.
Res. 2004, 37, 526 and references cited therein.
[3] a) A. P. Wight, M. E. Davis, Chem. Rev. 2002, 102,
3589; b) D. E. De Vos, M. Dams, B. F. Sels, P. A.
Jacobs, Chem. Rev. 2002, 102, 3615 and references cited
therein.
[4] a) K. Yamaguchi, C. Yoshida, S. Uchida, N. Mizuno, J.
Am. Chem. Soc. 2005, 127, 530; b) J. Kasai, Y. Nakaga-
wa, S. Uchida, K. Yamaguchi, N. Mizuno, Chem. Eur. J.
2006, 4176.
[10] R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schu-
chardt, Acc. Chem. Res. 1998, 31, 485.
[5] R. J. H. Gregory, Chem. Rev. 1999, 99, 3649 and refer-
ences cited therein.
[11] Examples ofepoxidation ofelectron-deifcient oleifns:
a) T. Honma, M. Nakajo, T. Mizugaki, K. Ebitani, K.
Kaneda, Tetrahedron Lett. 2002, 43, 6229; b) J. M.
Fraile, J. I. Garcꢁa, J. A. Mayoral, S. Sebti, R. Tahir,
Green Chem. 2001, 3, 271; c) C. Baccin, A. Gusso, F.
Pinna, G. Strukul, Organometallics 1995, 14, 1161; d) C.
Cativiela, F. Figueras, J. M. Fraile, J. I. Garcꢁa, J. A.
Mayoral, Tetrahedron Lett. 1995, 36, 4125.
[6] a) R. Noyori, S. Murata, M. Suzuki, Tetrahedron 1981,
37, 3899; b) W. J. Greenlee, D. G. Hangauer, Tetrahe-
dron Lett. 1983, 24, 4559; c) A. E. Vougioukas, H. B.
Kagan, Tetrahedron Lett. 1987, 28, 5513; d) S. Kobaya-
shi, T. Tsuchiya, T. Mukaiyama, Chem. Lett. 1991, 537;
e) J. K. Whitesell, R. Apodaca, Tetrahedron Lett. 1996,
37, 5513; f) H. S. Wilkinson, P. T. Grover, C. P. Vanden-
bossche, R. P. Bakale, N. N. Bhongle, S. A. Wald, C. H.
Senanayake, Org. Lett. 2001, 3, 553; g) I. S. Kruchok,
I. I. Gerus, V. P. Kukhar, Tetrahedron 2000, 56, 6533;
h) J. J. Song, F. Gallou, J. T. Reeves, Z. Tan, N. K. Yee,
C. H. Senanayake, J. Org. Chem. 2006, 71, 1273.
[12] Purification of Laboratory Chemicals, 3rd edn., (Eds.:
D. D. Perrin, W. L. F. Armarego), Pergamon Press,
Oxford, U. K., 1988.
[13] R. Mueller, H. K. Kammler, K. Wegner, S. E. Pratsinis,
Langmuir 2003, 19, 160.
1520
ꢀ 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2006, 348, 1516 – 1520