Chemoselective activation of aldimine in preference to aldehyde by the combination of BF3•OEt2 and water: Novel catalyst for the mannich-type reaction

Chemistry Letters

Volumn , Issue 9, 1999, Pages 947-948

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

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033474092     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.947     Document Type: Article

References (31)

1. R. Bloch, Chem. Rev., 98, 1407 (1998).
2. M. Yamaguchi, in "Comprehensive Organic Synthesis," ed by B. M. Trost and I. Fleming, Pergamon Press, Oxford (1991), Vol. 1, p. 325.
3. H. Nakamura, N. Asao, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 1273; H. Nakamura, H. Iwama, and Y. Yamamoto, J. Am. Chem. Soc., 118, 6641 (1996).
4. H. Nakamura, N. Asao, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 1273; H. Nakamura, H. Iwama, and Y. Yamamoto, J. Am. Chem. Soc., 118, 6641 (1996).
5. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi, Eur. J. Org. Chem, 15 (1999); S. Kobayashi, Chem. Soc. Rev., 28, 1 (1999).
6. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi, Eur. J. Org. Chem, 15 (1999); S. Kobayashi, Chem. Soc. Rev., 28, 1 (1999).
7. S. Kobayashi, Synlett, 1994, 689; S. Kobayashi, Eur. J. Org. Chem, 15 (1999); S. Kobayashi, Chem. Soc. Rev., 28, 1 (1999).
8. S. Kobayashi, Eur. J. Org. Chem 1999, 15; S. Kobayashi, T. Busujima, and S. Nagayama, Synlett, 1999, 545. See also references cited therein.
9. S. Kobayashi, Eur. J. Org. Chem 1999, 15; S. Kobayashi, T. Busujima, and S. Nagayama, Synlett, 1999, 545. See also references cited therein.
10. S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
11. S. Kobayashi and S. Nagayama, J. Org. Chem., 62, 232 (1997); S. Kobayashi and S. Nagayama, J. Am. Chem. Soc., 119, 10049 (1997).
12. T. Akiyama and J. Iwai, Synlett, 1998, 273.
13. Selected examples of Mannich-type reactions; a) I. Ojima, K. Yoshida, and S. Inaba, Chem. Lett., 1977, 429.
14. b) M. Onaka, R. Ohno, N. Yanagiya, and Y. Izumi, Synlett, 1993, 141.
15. c) K. Ishihara, M. Miyata, K. Hattori, T. Tada, and H. Yamamoto, J. Am. Chem. Soc., 116, 10520 (1994).
16. d) K. Ishihara, M. Funahashi, N. Hanaki, M. Miyata, and H. Yamamoto, Synlett, 1994, 963.
17. e) D. Ferraris, B. Young, T. Dudding, and T. Lectka, J. Am. Chem. Soc., 120, 4548 (1998).
18. f) M. Arend, B. Westermann, and N. Risch, Angew. Chem., Int. Ed. Engl., 37, 1044 (1998).
19. g) A. Fujii, E. Hagiwara, and M. Sodeoka, J. Am. Chem. Soc., 121, 5450 (1999).
20. H. C. Aspinall, N. Greeves, and E. G. McIver, Tetrahedron Lett., 39, 9283 (1998); K. Manabe and S. Kobayashi, Tetrahedron Lett., 40, 3773 (1999).
21. H. C. Aspinall, N. Greeves, and E. G. McIver, Tetrahedron Lett., 39, 9283 (1998); K. Manabe and S. Kobayashi, Tetrahedron Lett., 40, 3773 (1999).
22. Activation of imines by the combination of Lewis acid and protic acid, see; K. M. Ryan, R. A. Reamer, R. P. Volante, and I. Shinkai, Tetrahedron Lett., 28, 2103 (1987).
23. S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Otto, G. Boccaletti, and J. B. F. N. Engberts, J. Am. Chem. Soc., 120, 4238 (1998); S. Kobayashi, S. Nagayama, and T. Busujima, Chem. Lett., 1999, 71.
24. S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Otto, G. Boccaletti, and J. B. F. N. Engberts, J. Am. Chem. Soc., 120, 4238 (1998); S. Kobayashi, S. Nagayama, and T. Busujima, Chem. Lett., 1999, 71.
25. S. Kobayashi and I. Hachiya, J. Org. Chem., 59, 3590 (1994); S. Otto, G. Boccaletti, and J. B. F. N. Engberts, J. Am. Chem. Soc., 120, 4238 (1998); S. Kobayashi, S. Nagayama, and T. Busujima, Chem. Lett., 1999, 71.
26. 2. Formation of 2 was not observed in both cases.
27. 2O might be the reactive species.
28. When 1.5 equiv of ketene silyl acetal was employed, the adduct was obtained in 59% yield.
29. F. A. Cotton and G. Wilkinson, "Advanced Inorganic Chemistry," 5th ed, John Wiley & Sons, New York (1986), p. 174.
30. T. Akiyama, J. Takaya, and H. Kagoshima, Synlett, 1999, 1045.
31. It is known that a combination of Lewis acid and a Brønsted acid generates fairly strong acid. See; K. Tanabe and R. Noyori, "Super Strong acid and Super Strong Base," Kodansha-Scientific, Tokyo (1980).