Asymmetric intramolecular aldol reaction mediated by (S)-N-substituted-N- (2-pyrrolidinylmethyl)amine to prepare Wieland-Miescher ketone

Heterocycles

Volumn 82, Issue 2, 2010, Pages 1727-1737

  Akahane, Yuichi ^a   Inomata, Kohei ^a   Endo, Yasuyuki ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79952766416     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-10-S(E)119     Document Type: Article

References (79)

1. (a) P. Wieland and K. Miescher, Helv. Chim. Acta, 1950, 33, 2215;
2. (b) S. Ramachandran and M. S. Newman, Organic Syntheses, 1961, 41, 38;
3. (c) J. Gutzwiller, P. Buchschacher, and A. Fürst, Synthesis, 1977, 167;
4. (d) R. Uma, S. Swaminathan, and K. Rajagopalan, Tetrahedron Lett, 1984, 25, 5825;
5. (e) G. Ottolina, G. Gonzalo, G. Carrea, and B. Danieli, Adv. Synth. Catal, 2005, 347, 1035;
6. (f) Y. Kasai, K. Shimanuki, S. Kuwahara, M. Watanabe, and N. Harada, Chirality, 2006, 18, 177.
7. Recent applications of 2: (a) N. Shah and T. S. Scanlan, Bioorg. Med. Chem. Lett, 2004, 14, 5199;
8. (b) S. Díaz, A González, B. Bradshaw, J. Cuesta, and J. Bonjoch, J. Org. Chem, 2005, 70, 3749;
9. (c) H. Liu, D. R. Siegel, and S. J. Danishefsky, Org. Lett, 2006, 8, 423;
10. (d) A. B. Smith III, L. Kürti, A. H. Davulcu, and Y. S. Cho, Org. Process Res. Dev., 2007, 11, 19;
11. (e) K. P. Kaliappan and V. Ravikumar, Org. Lett, 2007, 9, 2417;
12. (f) B. Bradshaw, G. Etxebarria-Jardí, and J. Bonjoch, Org. Biomol. Chem, 2008, 6, 772;
13. (g) K. Ma, C. Zhang, M. Liu, Y. Chu, L. Zhou, C. Hu, and D. Ye, Tetrahedron Lett, 2010, 51, 1870.
14. (a) Z. G. Hajos and D. R. Parrish, German Patent DE 2102623, 1971;
15. (b) U. Eder, G. Sauer and R. Wiechert, German Patent DE 2014757, 1971;
16. (c) U. Eder, G. Sauer, and R. Wiechert, Angew. Chem., 1971, 83, 492;
17. (d) Z. G. Hajos and D. R. Parrish J. Org. Chem, 1973, 38, 3239;
18. (e) Z. G. Hajos and D. R. Parrish, J. Org. Chem, 1974, 39, 1615;
19. (f) R. A. Micheli, Z. G. Hajos, N. Cohen, D. R. Parrish, L. A. Portland, W. Sciamanna, M. A. Scott, and P. A. Wehri, J. Org. Chem, 1975, 40, 675;
20. (g) P. Buchschacher and A. Fuerst, Organic Syntheses, 1985, 63, 37;
21. (h) Z. G. Hajos and D. R. Parrish, Organic Syntheses, Collect. Vol. VII, p. 363, Wiley: New York, 1990;
22. (i) N. Harada, T. Sugioka, H. Uda, and T. Kuriki, Synthesis, 1990, 53;
23. (j) D. Rajagopal, K. Rajagopalan, and S. Swaminathan, Tetrahedron: Asymmetry, 1996, 7, 2189;
24. (k) T. Bui and C. F. Barbas III, Tetrahedron Lett., 2000, 41, 6951;
25. (l) D. Rajagopal, R. Narayanan, and S. Swaminathan, Tetrahedron Lett, 2001, 42, 4887.
26. (a) G. Zhong, T. Hoffmann, R. A. Lerner, S. Danishefsky, and C. F. Barbas III, J. Am. Chem. Soc., 1997, 119, 8131;
27. (b) K. Fuhshuku, N. Funa, T. Akeboshi, H. Ohta, H. Hosomi, S. Ohba, and T. Sugai, J. Org. Chem, 2000, 65, 129;
28. (c) H. Hioki, T. Hashimoto, and M. Kodama, Tetrahedron: Asymmetry, 2000, 11, 829;
29. (d) A. Gassama, J. d'Angelo, C. Cavé, J. Mahuteau, and C. Riche, Eur. J. Org. Chem, 2000, 3165;
30. (e) S. G. Davies, R. L. Sheppard, A. D. Smith, and J. E. Thomson, Chem. Commun, 2005, 3802;
31. (f) M. Hosseini, N. Stiasni, V. Barbieri, and C. O. Kappe, J. Org. Chem, 2007, 72, 1417;
32. (g) S. Sulzer-Mossé, M. Laars, K. Kriis, T. Kanger, and A. Alexakis, Synthesis, 2007, 1729;
33. (h) B. Bradshaw, G. Etxebarria-Jardi, J. Bonjoch, S. F. Viózquez, G. Guillena, and C. Nájera, Adv. Synth. Catal, 2009, 351, 2842;
34. (i) Á. L. Fuentes de Arriba, L. Simón, C. Raposo, V. Alcázar, and J. R. Morán, Tetrahedron, 2009, 65, 4841;
35. (j) K. Mori, T. Katoh, T. Suzuki, T. Noji, M. Yamanaka, and T. Akiyama, Angew. Chem. Int. Ed, 2009, 48, 9652.
36. (a) K. L. Brown, L. Damm, J. D. Dunitz, A. Eschenmoser, R. Hobi, and C. Kratky, Helv. Chim. Acta, 1978, 61, 3108;
37. (b) C. Agami and H. Sevestre, J. Chem. Soc., Chem. Commun., 1984, 1385;
38. (c) C. Agami, C. Puchot, and H. Sevestre, Tetrahedron Lett, 1986, 27, 1501;
39. (d) C. Agami and C. Puchot, J. Mol. Catal, 1986, 38, 341;
40. (e) C. Agami, N. Platzer, and H. Sevestre, Bull. Soc. Chim. Fr, 1987, 358;
41. (f) C. Agami, Bull. Soc. Chim. Fr, 1988, 499;
42. (g) N. Gathaergood, Aust. J. Chem, 2002, 55, 615.
43. (a) S. Bahmanyar and K. N. Houk, J. Am. Chem. Soc, 2001, 123, 11273;
44. (b) S. Bahmanyar and K. N. Houk, J. Am. Chem. Soc, 2001, 123, 12911;
45. (c) L. Hoang, S. Bahmanyar, K. N. Houk, and B. List, J. Am. Chem. Soc, 2003, 125, 16;
46. (d) S. Bahmanyar, K. N. Houk, H. J. Martin, and B. List, J. Am. Chem. Soc., 2003, 125, 2475;
47. (e) B. List, L. Hoang, and H. J. Martin, Proc. Vat. Acad. Sci. U. S. A., 2004, 101, 5839;
48. (f) B. List, Acc. Chem. Res., 2004, 37, 548;
49. (g) C. Allemann, R. Gordillo, F. R. Clemente, P. H.-Y. Cheong, and K. N. Houk, Acc. Chem. Res, 2004, 37, 558;
50. (h) P. H.-Y. Cheong and K. N. Houk, Synthesis, 2005, 1533.
51. For reviews: (a) B. List, Tetrahedron, 2002, 58, 5573;
52. (b) W. Notz, F. Tanaka, and C. F. Barbas III, Acc. Chem. Res., 2004, 37, 580;
53. (c) P. I. Dalko and L. Moisan, Angew. Chem. Int. Ed., 2004, 43, 5138;
54. (d) A. Berkessel and H. Gröger, Asymmetric Organocatalysis, Wiley-VCH: Weinheim, 2005;
55. (e) B. List, Chem. Commun, 2006, 819;
56. (f) H. Pellissier, Tetrahedron, 2007, 63, 9267;
57. (g) G. Guillena, C. Nájera, and D. J. Ramón, Tetrahedron: Asymmetry, 2007, 18, 2249;
58. (h) A. Dondoni and A. Massi, Angew. Chem. Int. Ed., 2008, 47, 4638;
59. (i) P. Melchiorre, M. Marigo, A. Carlone, and G. Bartoli, Angew. Chem. Int. Ed., 2008, 47, 6138.
60. (a) S. Saito, M. Nakadai, and H. Yamamoto, Synlett, 2001, 1245;
61. (b) M. Nakadai, S. Saito, and H. Yamamoto, Tetrahedron, 2002, 58, 8167;
62. (c) S. Saito and H. Yamamoto, Acc. Chem. Res., 2004, 37, 570;
63. (d) S. Saito, N. Momiyama, and H. Yamamoto, J. Synth. Org. Chem. Jpn., 2008, 66, 774.
64. Some selected examples: (a) K. Ishihara and K. Nakano, J. Am. Chem. Soc., 2005, 127, 10504 and 13079;
65. (b) A. Sakakura, K. Suzuki, K. Nakano, and K. Ishihara, Org. Lett, 2006, 8, 2229;
66. (c) A. Sakakura, K. Suzuki, and K. Ishihara, Adv. Synth. Catal, 2006, 348, 2457;
67. (d) H. Sundén, R. Rios, Y. Xu, L. Eriksson, and A. Córdova, Adv. Synth. Catal, 2007, 349, 2549.
68. Some selected examples: (a) S. Mossé, M. Laars, M. Kriis, T. Kanger, and A. Alexakis, Org. Lett., 2006, 8, 2559;
69. (b) S. Mossé and A. Alexakis, Chem. Commun, 2007, 3123;
70. (c) H. Chen, Y. Wang, S. Wei, and J. Sun, Tetrahedron: Asymmetry, 2007, 18, 1308;
71. (d) D. A. Alonso, S. Kitagaki, N. Usumi, and C. F. Barbas III, Angew. Chem. Int. Ed., 2008, 47, 4588.
72. (a) T. Kanger, K. Kriis, M. Laars, T. Kailas, A-M. Müürisepp, T. Pehk, and M. Lopp, J. Org. Chem., 2007, 72, 5168;
73. (b) E. Lacoste, E. Vaique, M. Berlande, I. Pianet, J.-M. Vincent, and Y. Landais, Eur. J. Org. Chem, 2007, 167;
74. (c) M. Laars, K. Kriis, T. Kailas, A.-M. Müürisepp, T. Pehk, T. Kanger, and M. Lopp, Tetrahedron: Asymmetry, 2008, 19, 641.
75. Y. Akahane, N. Inage, T. Nagamine, K. Inomata, and Y. Endo, Heterocycles, 2007, 74, 637.
76. Y. Akahane, K. Inomata, and Y. Endo, Heterocycles, 2009, 77, 1065.
77. K. Iseki, Y. Kuroki, M. Takahashi, S. Kishimoto, and Y. Kobayashi, Tetrahedron, 1997, 53, 3513.
78. M. Asami, H. Ohno, S. Kobayashi, and T. Mukaiyama, Bull. Chem. Soc. Jpn, 1978, 51, 1869.
79. J. L. Olivares-Romero and E. Juaristi, Tetrahedron, 2008, 64, 9992.