Mannich-Type Reaction with Trifluoromethylated N,O-Hemiacetal: Facile Preparation of β-Amino-β-trifluoromethyl Carbonyl Compounds

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1577-1579

  Takaya, Jun ^a   Kagoshima, Hirotaka ^a   Akiyama, Takahiko ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001125869     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005812e     Document Type: Article

References (28)

1. Fluoroorganic Chemistry. Synthetic Challenge and Biomedicinal Rewards, Tetrahedron Symposia in Print No. 58. Resnati, G.; Soloshonok, V. A., Eds. Tetrahedron 1996, 52, 1-300.
2. (a) Costerousse, G.; Teutsch, G. Tetrahedron 1986, 42, 2685.
3. (b) Fuchigami, T.; Nakagawa, Y.; Nonaka, T. J. Org. Chem. 1987, 52, 5489.
4. (c) Fuchigami, T.; Ichikawa, S.; Konno, A. Chem. Lett. 1989, 1987.
5. (d) Ishii, A.; Higashiyama, K.; Mikami, K. Synlett 1997, 1381.
6. (e) Ishii, A.; Miyamoto, F.; Higashiyama, K.; Mikami, K. Tetrahedron Lett. 1998, 39, 1199.
7. Xu, Y.; Dolbier, W. R., Jr. Tetrahedron Lett. 1998, 39, 9151.
8. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
9. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
10. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
11. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
12. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
13. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
14. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
15. For the use of trifluoroacetaldehyde ethyl hemiacetal as a starting material for the trifluoromethylated compounds, see: Kubota, T.; Iijima, M.; Tanaka, T. Tetrahedron Lett. 1992, 33, 1351. Funabiki, K.; Nojiri, M.; Matsui, M.; Shibata, K. J. Chem. Soc., Chem. Commun. 1998, 2051. Funabiki, K.; Matsunaga, K.; Matsui, M.; Shibata, K. Synlett 1999, 1477. Loh, T.-P.; Li, X.-R. Tetrahedron 1999, 55, 5611. Kumadaki, I.; Jonoshita, S.; Harada, A.; Omote, M.; Ando, A. J. Fluorine Chem. 1999, 97, 61. Sakuma, K.; Kuki, N.; Kumo, T.; Takagi, T.; Koyama, M.; Ando, A.; Kumadaki, I. J. Fluorine Chem. 1999, 93, 165. Gong, Y.; Kato, K.; Kimoto, H, Synlett 1999, 1403. Ishii, A.; Mikami, K. J. Synth. Org. Chem. Jpn. 2000, 58, 324.
16. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1045. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1426. Akiyama, T.; Takaya, J.; Kasoshima, H. Chem. Lett. 1999, 947. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
17. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1045. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1426. Akiyama, T.; Takaya, J.; Kasoshima, H. Chem. Lett. 1999, 947. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
18. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1045. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1426. Akiyama, T.; Takaya, J.; Kasoshima, H. Chem. Lett. 1999, 947. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
19. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1045. Akiyama, T.; Takaya, J.; Kagoshima, H. Svnlett 1999, 1426. Akiyama, T.; Takaya, J.; Kasoshima, H. Chem. Lett. 1999, 947. Akiyama, T.; Takaya, J.; Kagoshima, H. Tetrahedron Lett. 1999, 40, 7831.
20. Akiyama, T.; Iwai, J. Synlett 1998, 273. Akiyama, T.; Iwai, J.; Onuma, Y.; Kagoshima, H. J. Chem. Soc., Chem. Commun. 1999, 2191.
21. Akiyama, T.; Iwai, J. Synlett 1998, 273. Akiyama, T.; Iwai, J.; Onuma, Y.; Kagoshima, H. J. Chem. Soc., Chem. Commun. 1999, 2191.
22. 2b
23. For the use of N,O-hemiacetal in Mannich-type reactions, see: Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. Ferraris, D.; Young, B.; Dudding, T.; Drury, W. J., III; Lectka, T. Tetrahedron 1999, 55, 8869.
24. For the use of N,O-hemiacetal in Mannich-type reactions, see: Ferraris, D.; Dudding, T.; Young, B.; Drury, W. J., III; Lectka, T. J. Org. Chem. 1999, 64, 2168. Ferraris, D.; Young, B.; Dudding, T.; Drury, W. J., III; Lectka, T. Tetrahedron 1999, 55, 8869.
25. Abouabdellah, A.; Bégué, J.-P.; Bonnet-Delpon, D.; Nga, T. T. T. J. Org. Chem. 1997, 62, 8826.
26. 3 as a promoter, see: Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313. Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074.
27. 3 as a promoter, see: Yamaguchi, M.; Kido, Y.; Hayashi, A.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1313. Yamaguchi, M.; Tsukagoshi, T.; Arisawa, M. J. Am. Chem. Soc. 1999, 121, 4074.
28. Kohayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.