Mannich-type reaction of N,O-acetals with ketones mediated by a combination of TiCl4 and PhSiCl3

Heterocycles

Volumn 82, Issue 1, 2010, Pages 325-332

  Kamogawa, Satoshi ^a   Ikeda, Takashi ^a   Kuriyama, Masami ^a   Matsumura, Yoshihiro ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79751493538     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-09-S(E)2     Document Type: Article

References (42)

1. T. Shono, H. Hamaguchi, and Y. Matsumura, J. Am. Chem. Soc., 1975, 97, 4264;
2. T. Iwasaki, H. Horikawa, K. Matsumoto, and M. Miyoshi, J. Org. Chem., 1979, 44, 1552;
3. T. Shono, Y. Matsumura, O. Onomura, M. Ogaki, and K. Kanazawa, J. Org. Chem., 1987, 52, 536;
4. G. N. Wanyoike, O. Onomura, T. Maki, and Y. Matsumura, Org. Lett., 2002, 4, 1875;
5. S. S. Libendi, Y. Demizu, Y. Matsumura, and O. Onomura, Tetrahedron, 2008, 64, 3935;
6. G. N. Wanyoike, Y. Matsumura, and O. Onomura, Heterocycles, 2009, 79, 339.
7. Recent representative reviews, see:
8. W. C. Speckamp, and M. J. Moolenaar, Tetrahedron, 2000, 56, 3817;
9. A. Yazici, and S. G. Pyne, Synthesis, 2009, 339;
10. A. Yazici, and S. G. Pyne, Synthesis, 2009, 513.
11. Some literatures, see:
12. S. Yamasaki, T. Iida, and M. Shibasaki, Tetrahedron Lett., 1999, 40, 307;
13. G. R. Humphrey, R. A. Miller, P. J. Pye, K. Rossen, R. A. Reamer, A. Maliakal, S. S. Ceglia, E. J. J. Grabowski, R. P. Volante, and P. J. Reider, J. Am. Chem. Soc., 1999, 121, 11261;
14. Y. Matsumura, Y. Kanda, K. Shirai, O. Onomura, and T. Maki, Org. Lett., 1999, 1, 175;
15. O. Onomura, Y. Kanda, Y. Nakamura, T. Maki, and Y. Matsumura, Tetrahedron Lett., 2002, 43, 3229;
16. Y. Matsumura, T. Ikeda, and O. Onomura, Heterocycles, 2006, 67, 113;
17. Y. Matsumura, D. Minato, and O. Onomura, J. Organomet. Chem., 2007, 692, 654.
18. T. Shono, Y. Matsumura, and K. Tsubata, J. Am. Chem. Soc., 1981, 103, 1172.
19. O. Okitsu, R. Suzuki, and S. Kobayashi, J. Org. Chem., 2001, 66, 809;
20. O. Onomura, T. Ikeda, and Y. Matsumura, Heterocycles, 2005, 66, 81.
21. 3SiCl promoted aldol reaction, see:
22. 2 catalyzed aldol reaction, see:
23. S. Kobayashi, and K. Nishio, J. Org. Chem., 1993, 58, 2647;
24. 4, see:
25. S. Kotani, Y. Shimoda, M. Sugiura, and M. Nakajima, Tetrahedron Lett., 2009, 50, 4602.
26. 3 reported by us, see:
27. F. Iwasaki, O. Onomura, K. Mishima, T. Maki, and Y. Matsumura, Tetrahedron Lett., 1999, 40, 7507;
28. F. Iwasaki, O. Onomura, K. Mishima, T. Kanematsu, T. Maki, and Y. Matsumura, Tetrahedron Lett., 2001, 42, 2525;
29. O. Onomura, Y. Kouchi, F. Iwasaki, and Y. Matsumura, Tetrahedron Lett., 2006, 47, 3751;
30. Y. Matsumura, K. Ogura, Y. Kouchi, F. Iwasaki, and O. Onomura, Org. Lett., 2006, 17, 3789;
31. O. Onomura, P. G. Kirira, T. Tanaka, S. Tsukada, Y. Matsumura, and Y. Demizu, Tetrahedron, 2008, 64, 7498;
32. R. Šebesta, M. Mečiarová, E. Molnár, J. Czismadiová, P. Fodran, O. Onomura, and Š. Toma, J. Organomet. Chem., 2008, 693, 3131.
33. 3 (1.0 equiv).
34. 2 column chromatography. Also, the diastereomer ratio of 11 could not be determined by NMR, HPLC or GC. Similarly, the diastereomer ratio of 14 could not be determined.
35. 3.
36. Recent examples, see: U. Albrecht, H. Armbrust, P. Langer, Synlett, 2004, 143;
37. Y. Demizu, H. Shiigi, T. Oda, Y. Matsumura, and O. Onomura, Tetrahedron Lett., 2008, 49, 48;
38. H. Shiigi, H. Mori, T. Tanaka, Y. Demizu, and O. Onomura, Tetrahedron Lett., 2008, 49, 5247;
39. Y. Demizu, H. Shiigi, H. Mori, K. Matsumoto, and O. Onomura, Tetrahedron: Asymmetry, 2008, 19, 2659;
40. T. Nagase, T. Takahashi, T. Sasaki, A. Nagumo, K. Shimamura, Y. Miyamoto, H. Kitazawa, M. Kanesaka, R. Yoshimoto, K. Aragane, S. Tokita, and N. Sato, J. Med. Chem., 2009, 52, 4111;
41. M. Shibuya, M. Tomizawa, Y. Sasano, and Y. Iwabuchi, J. Org. Chem., 2009, 74, 4619.
42. T. Momose, M. Toshima, N. Toyooka, Y. Hirai, and C. H. Eugster, J. Chem. Soc, Perkin Trans. 1, 1997, 1307.