Brønsted Acid-Catalyzed Mannich-Type Reactions in Aqueous Media

Advanced Synthesis and Catalysis

Volumn 344, Issue 3-4, 2002, Pages 338-347

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

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

Aldimine; Br nsted acid; Mannich type reaction; Water as solvent

Indexed keywords

EID: 0000049512     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200206)344:3/4<338::AID-ADSC338>3.0.CO;2-O     Document Type: Article

References (58)

1. P. G. Jessop, T. Ikariya, R. Noyori, Chem. Rev. 1999, 99, 475-493; P. E. Savage, Chem. Rev. 1999, 99, 603-621.
2. P. G. Jessop, T. Ikariya, R. Noyori, Chem. Rev. 1999, 99, 475-493; P. E. Savage, Chem. Rev. 1999, 99, 603-621.
3. D. P. Curran, Pure Appl. Chem. 2000, 72, 1649-1653.
4. T. Welton, Chem. Rev. 1999, 99, 2071-2083.
5. K. Tanaka, F. Toda, Chem. Rev. 2000, 100, 1025-1074.
6. a) H.-U. Reissig, in Organic Synthesis Highlights; VCH, Weinheim, 1991, pp. 71;
7. b) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035;
8. c) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley, New York, 1997;
9. d) A. Lubineau, J. Augé, Y. Queneau, Synthesis 1994, 741-760;
10. d) C.-J. Li, Tetrahedron 1996, 52, 5643-5668;
11. e) P. Grieco, (Ed.), Organic Reactions in Water, Blackie Academic & Professional, London, 1998.
12. A. V. Bordunov, J. S. Bradshaw, V. N. Pastushok, R. M. Izatt, Synlett 1996, 933.
13. a) E. F. Kleinman, R. A. Volkmann, in Comprehensive Organic Synthesis, Vol. 2, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 975-1006;
14. b) L. E. Overman, D. J. Ricca, in Comprehensive Organic Synthesis, Vol. 2, (Eds.: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 1007-1046.
15. a) I. Ojima, S. Inaba, K. Yoshida, Tetrahedron Lett. 1977, 3643-3646;
16. b) R. A. Pilli, D. Russowsky, J. Chem. Soc. Chem. Commun. 1987, 1053-1054;
17. c) G. Guanti, E. Narisano, L. Banfi, Tetrahedron Lett. 1987, 28, 4331-4334;
18. d) T. Mukaiyama, K. Kashiwagi, S. Matsui, Chem. Lett. 1989, 1397-1400;
19. e) T. Mukaiyama, H. Akamatsu, J. S. Han, Chem. Lett. 1990, 889-892;
20. f) M. Onaka, R. Ohno, N. Yanagiya, Y. Izumi, Synlett 1993, 141-142;
21. f) K. Ishihara, K. Funahashi, N. Hanaki, M. Miyata, H. Yamamoto, Synlett 1994, 963-964;
22. g) K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524; R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 184-187; M. Shimizu, S. Itohara, Synlett 2000, 1828-1830.
23. g) K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524; R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 184-187; M. Shimizu, S. Itohara, Synlett 2000, 1828-1830.
24. g) K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524; R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 184-187; M. Shimizu, S. Itohara, Synlett 2000, 1828-1830.
25. a) M. Arend, B. Westermann, N. Risch, Angew. Chem. Int. Ed. 1998, 37, 1044-1070;
26. b) M. Arend, Angew. Chem. Int. Ed. 1999, 38, 2873-2874;
27. c) E. Hagiwara, A. Fujii, M. Sodeoka, J. Am. Chem. Soc. 1998, 120, 2474-2475;
28. d) D. Ferraris, B. Young, C. Cox, W. J. D. III, T. Dudding, T. Lectka, J. Org. Chem. 1998, 63, 6090-6091;
29. e) R. Müller, H. Goesmann, H. Waldmann, Angew. Chem. Int. Ed. 1999, 38, 184-187;
30. f) H. Ishitani, M. Ueno, S. Kobayashi, J. Am. Chem. Soc. 2000, 122, 8180-8186;
31. g) K. Juhl, N. Gathergood, K. A. Jørgensen, Angew. Chem. Int. Ed. 2001, 40, 2995-2997;
32. h) B. List, J. Am. Chem. Soc. 2000, 122, 9336-9337;
33. i) W. Notz, K. Sakthivel, T. Bui, G. Zhong, I. C. F. Barbas, Tetrahedron Lett. 2001, 42, 199-201.
34. F. F. Blicke, Org. React. (N. Y.) 1942, 1, 303-341.
35. S. Kobayashi, Eur. J. Org. Chem. 1999, 15-27.
36. T.-P. Loh, S. B. K. W. Liung, K.-L. Tan, L.-L. Wei, Tetrahedron 2000, 56, 3227-3237.
37. S. Kobayashi, T. Busujima, S. Nagayama, Synlett 1999, 545-546; S. Kobayashi, H. Ishitani, J. Chem. Soc. Chem. Commun. 1995, 1379; K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. Int. Ed. 2000, 39, 1958-1960.
38. S. Kobayashi, T. Busujima, S. Nagayama, Synlett 1999, 545-546; S. Kobayashi, H. Ishitani, J. Chem. Soc. Chem. Commun. 1995, 1379; K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. Int. Ed. 2000, 39, 1958-1960.
39. S. Kobayashi, T. Busujima, S. Nagayama, Synlett 1999, 545-546; S. Kobayashi, H. Ishitani, J. Chem. Soc. Chem. Commun. 1995, 1379; K. Miura, K. Tamaki, T. Nakagawa, A. Hosomi, Angew. Chem. Int. Ed. 2000, 39, 1958-1960.
40. T. Akiyama, M. Suzuki, J. Chem. Soc. Chem. Commun. 1997, 2357-2358; T. Akiyama, J. Iwai, Synlett 1998, 273-274; T. Akiyama, J. Iwai, Y. Onuma, H. Kagoshima, J. Chem. Soc. Chem. Commun. 1999, 2191-2192; T. Akiyama, M. Sugano, H. Kagoshima, Tetrahedron Lett. 2001, 42, 3889-3892.
41. T. Akiyama, M. Suzuki, J. Chem. Soc. Chem. Commun. 1997, 2357-2358; T. Akiyama, J. Iwai, Synlett 1998, 273-274; T. Akiyama, J. Iwai, Y. Onuma, H. Kagoshima, J. Chem. Soc. Chem. Commun. 1999, 2191-2192; T. Akiyama, M. Sugano, H. Kagoshima, Tetrahedron Lett. 2001, 42, 3889-3892.
42. T. Akiyama, M. Suzuki, J. Chem. Soc. Chem. Commun. 1997, 2357-2358; T. Akiyama, J. Iwai, Synlett 1998, 273-274; T. Akiyama, J. Iwai, Y. Onuma, H. Kagoshima, J. Chem. Soc. Chem. Commun. 1999, 2191-2192; T. Akiyama, M. Sugano, H. Kagoshima, Tetrahedron Lett. 2001, 42, 3889-3892.
43. T. Akiyama, M. Suzuki, J. Chem. Soc. Chem. Commun. 1997, 2357-2358; T. Akiyama, J. Iwai, Synlett 1998, 273-274; T. Akiyama, J. Iwai, Y. Onuma, H. Kagoshima, J. Chem. Soc. Chem. Commun. 1999, 2191-2192; T. Akiyama, M. Sugano, H. Kagoshima, Tetrahedron Lett. 2001, 42, 3889-3892.
44. 4.
45. A. H. Blatt, N. Gross, J. Org. Chem. 1964, 29, 3306-3311.
46. Preliminary communications: T. Akiyama, J. Takaya, H. Kagoshima, Synlett 1999, 1045-1048; T. Akiyama, J. Takaya, H. Kagoshima, Synlett 1999, 1426-1428.
47. Preliminary communications: T. Akiyama, J. Takaya, H. Kagoshima, Synlett 1999, 1045-1048; T. Akiyama, J. Takaya, H. Kagoshima, Synlett 1999, 1426-1428.
48. T. Akiyama, J. Takaya, H. Kagoshima, Tetrahedron Lett. 1999, 40, 7831-7834; T. Akiyama, J. Takaya, H. Kagoshima, Tetrahedron Lett. 2001, 42, 4025-4028.
49. T. Akiyama, J. Takaya, H. Kagoshima, Tetrahedron Lett. 1999, 40, 7831-7834; T. Akiyama, J. Takaya, H. Kagoshima, Tetrahedron Lett. 2001, 42, 4025-4028.
50. Kobayashi and co-workers independently reported Brønsted-surfactant combined catalyst at the same time; see: K. Manabe, Y. Mori, S. Kobayashi, Synlett 1999, 1401-1402; K. Manabe, S. Kobayashi, Org. Lett. 1999, 1, 1965-1967.
51. Kobayashi and co-workers independently reported Brønsted-surfactant combined catalyst at the same time; see: K. Manabe, Y. Mori, S. Kobayashi, Synlett 1999, 1401-1402; K. Manabe, S. Kobayashi, Org. Lett. 1999, 1, 1965-1967.
52. S. Kobayashi, S. Nagayama, J. Org. Chem. 1997, 62, 232-233; S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1997, 119, 10049-10053.
53. S. Kobayashi, S. Nagayama, J. Org. Chem. 1997, 62, 232-233; S. Kobayashi, S. Nagayama, J. Am. Chem. Soc. 1997, 119, 10049-10053.
54. H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641-6647.
55. T. Akiyama, J. Takaya, H. Kagoshima, Chem. Lett. 1999, 947-948; M. Shimizu, S. Itohara, Synlett 2000, 1828-1830.
56. T. Akiyama, J. Takaya, H. Kagoshima, Chem. Lett. 1999, 947-948; M. Shimizu, S. Itohara, Synlett 2000, 1828-1830.
57. K. Yonehara, K. Ohe, S. Uemura, J. Org. Chem. 1999, 64, 9381-9385.
58. K. Tanaka, R. Shiraishi, Green Chem. 2000, 272-273.