S. Matsukawa, M. Saijo / Tetrahedron Letters 49 (2008) 4655–4657
4657
4. Singh, R. P.; Robert, G. C.; Kirchmeier, L.; Shreeve, J. M. J. Org. Chem. 1999, 64,
2873.
5. Hagiwara, T.; Mochizuki, H.; Fuchikami, T. Synlett 1997, 869.
6. (a) Hagiwara, T.; Kobayashi, T.; Fuchikami, T. Main Group Chem. 1997, 2, 13; (b)
Mizuta, S.; Shibata, N.; Sato, T.; Fujimoto, H.; Nakamura, S.; Toru, T. Synlett
2006, 267.
7. (a) Prakash, G. K. S.; Mandal, M.; Panja, C.; Mathew, T.; Olah, G. A. J. Fluorine
Chem. 2003, 123, 61; (b) Prakash, G. K. S.; Panja, C.; Vaghoo, H.; Surampudi, V.;
Kultyshev, R.; Mandal, M.; Rasul, G.; Mathew, T.; Olah, G. A. J. Org. Chem. 2006,
71, 6806.
8. Song, J. J.; Tan, Z.; Reeves, J. T.; Gallou, F.; Yee, N. K.; Senanayake, C. H. Org. Lett.
2005, 7, 2193.
15. General experimental procedure for the trifluoromethylation of carbonyl
compounds: To a solution of appropriate carbonyl compound (1 mmol) and
TTMPP (0.05 mmol) in solvent (1 mL), TMSCF3 (1.5 mmol) was added at room
temperature. The reaction was monitored by TLC. Then, the mixture was
quenched with water and extracted with ether (2 ꢀ 25 mL). The combined
extracts were washed with water and brine, and then dried over Na2SO4. The
solvent was removed on an evaporator to leave crude product, which was
purified by column chromatography on silica gel (AcOEt/hexane = 1:5) to give
the corresponding product.
16. (a) Blazejewski, J. C.; Anselmi, E.; Wilmshurst, M. P. Tetrahedron Lett. 1999, 40,
5475; (b) Petrov, V. V. Tetrahedron Lett. 2000, 41, 6959; (c) Prakash, G. K. S.;
Mandal, M.; Schweizer, S.; Petasis, N. A.; Olah, G. A. Org. Lett. 2000, 2, 3173; (d)
Prakash, G. K. S.; Mandal, M.; Olah, G. A. Synlett 2001, 77; (e) Dilman, A. D.;
Arkhipov, D. E.; Levin, V. V.; Belyakov, P. A.; Korlyukov, A. A.; Struchkova, M. I.;
Tartakovsky, V. A. J. Org. Chem. 2007, 72, 8604.
9. Mukaiyama, T.; Kawano, Y.; Fujisawa, H. Chem. Lett. 2005, 34, 88.
10. Kawano, Y.; Kaneko, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 2006, 79, 1133.
11. Iwanami, K.; Oriyama, T. Synlett 2006, 112.
12. Wada, M.; Higashizaki, S. J. Chem. Soc., Chem. Commun. 1984, 482.
13. (a) Maddock, S. M.; Finn, M. G. Organometallics 2000, 19, 2684; (b) Yoshimoto,
K.; Kawabata, H.; Nakamichi, N.; Hayashi, M. Chem. Lett. 2001, 934; (c)
Kawabata, H.; Hayashi, M. Tetrahedron Lett. 2002, 43, 5645; (d) Röper, S.;
Wartchow, R.; Hoffmann, M. R. Org. Lett. 2002, 4, 3179; (e) Chuprakov, S.;
Malyshev, D. A.; Trofimov, A.; Gevorgyan, V. J. Am. Chem. Soc. 2007, 129, 14868;
(f) Weeden, J. A.; Chisholm, J. D. Tetrahedron Lett. 2007, 47, 9313.
14. (a) Matsukawa, S.; Okano, N.; Imamoto, T. Tetrahedron Lett. 2000, 41, 103; (b)
Matsukawa, S.; Obu, K. Chem. Lett. 2004, 1626; (c) Matsukawa, S.; Kitazaki, E.
Tetrahedron Lett. 2008, 49, 2982.
17. (a) Kawano, Y.; Fujisawa, H.; Mukaiyama, T. Chem. Lett. 2005, 34, 422; (b)
Prakash, G. K. S.; Mogi, R.; Olah, G. A. Org. Lett. 2006, 8, 3589.
18. General experimental procedure for the trifluoromethylation of imine: To a solution
of appropriate imine (1 mmol) and TTMPP (0.20 mmol) in DMPU (1,3-dimethyl-
3,4,5,6-tetrahydro-2(1H)-pyrimidinone) (1 mL), TMSCF3 (2.0 mmol) was added
at room temperature. The reaction was monitored by TLC. After 22 h, the
mixture was quenched with water and extracted with AcOEt (2 ꢀ 25 mL). The
combined extracts were washed with water and brine, and then dried over
Na2SO4. The solvent was removed on an evaporator to leave crude product,
which was purified by preparative TLC to afford the desired product.