Copper-catalyzed enantioselective intramolecular conjugate addition/trapping reactions: Synthesis of cyclic compounds with multichiral centers

Chemistry - A European Journal

Volumn 13, Issue 13, 2007, Pages 3765-3771

  Li, Kangying ^a   Alexakis, Alexandre ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Copper; Cyclization; Enolates; Michael addition; Selectivity

Indexed keywords

CATALYSIS; CYCLIZATION; ENANTIOSELECTIVITY; ORGANIC COMPOUNDS;

ENOLATES; HETEROCYCLIC COMPOUNDS; MICHAEL ADDITION;

COPPER;

EID: 34250380241     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601327     Document Type: Article

References (78)

1. For recent reviews on asymmetric conjugate addition: a) N. Krause, A. Hoffmann-Roder, Synthesis 2001, 171-196;
2. b) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033-8061;
3. c) M. Kanai, M. Shibasaki, Catalytic Asymmetric Synthesis (Ed.: I. Ojima), 2nd ed., Wiley, New York, 2000, p. 569.
4. For examples of the copper-catalyzed asymmetric conjugate addition of organozinc reagents: a) A. Alexakis, D. Polet, S. Rosset, S. March, J. Org. Chem. 2004, 69, 5660-5667;
5. b) A. Alexakis, C. Benhaim, Eur. J. Org. Chem. 2002, 3221-3236;
6. c) A. Alexakis, C. Benhaim, S. Rosset, M. Human, J. Am. Chem. Soc. 2002, 124, 5262-5263;
7. d) L. A. Arnold, R. Naasz, A. J. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2001, 123, 5841-5842;
8. e) A. Alexakis, G. P. Trevitt, G. Bernardinelli, J. Am. Chem. Soc. 2001, 123, 4358-4359;
9. f) A. Alexakis, J. Burton, J. Vastra, C. Benhaim, X. Fournioux, A. Van den Heuvel, J. M. Leveque, F. Maze, S. Rosset, Eur. J. Org. Chem. 2000, 4011-4027;
10. g) A. Alexakis, C. Benhaim, Org. Lett. 2000, 2, 2579-2581;
11. h) B. L. Feringa, Acc. Chem. Res. 2000, 33, 346-353;
12. i) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 50, 2879-2888;
13. j) M. Yan, A. S. C. Chan, Tetrahedron Lett. 1999, 40, 6645-6648;
14. k) S. J. Degrado, H. Mizutani, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 13362-13363.
15. For cyclic enones: a) M. d'Augustin, L. Palais, A. Alexakis, Angew. Chem. 2005, 117, 1400-1402;
16. Angew. Chem. Int. Ed. 2005, 44, 1376-1378;
17. b) L. Su, X. Li, W. L. Chan, X. Jia, A. S. C. Chan, Tetrahedron: Asymmetry 2003, 14, 1865-1869;
18. c) L. Liang, A. S. C. Chan, Tetrahedron: Asymmetry 2002, 13, 1393-1396;
19. d) M. Diegez, S. Deeremberg, O. Pamies, C. Claver, P. W. N. M. van Leeuwen, P. Kamer, Tetrahedron: Asymmetry 2000, 11, 3161-3166;
20. e) Y. Takemoto, S. Kuraoka, N. Hamaue, C. Iwata, Tetrahedron: Asymmetry 1996, 7, 993-996; for acyclic enones:
21. f) A. Alexakis, V. Albrow, K. Biswas, M. d'Augustin, O. Pireto, S. Woodward, Chem. Commun. 2005, 2843-2845;
22. g) P. K. Fraser, S. Woodward, Chem. Eur. J. 2003, 9, 776-783;
23. h) S. M. W. Bennett, S. M. Brown, J. P. Muxworthy, S. Woodward, Tetrahedron Lett. 1999, 40, 1767-1770; for nitro olefins:
24. i) D. Polet. A. Alexakis, Tetrahedron Lett. 2005, 46, 1529-1532;
25. j) U. Eilitz, F. Lessmann, O. Seidelmann, V. Wendisch, Tetrahedron: Asymmetry 2003, 14, 3095-3097.
26. For nitro olefins: a) A. Alexakis, D. Polet, C. Benhaim, S. Rosset, Tetrahedron: Asymmetry 2004, 15, 2199-2203;
27. b) A. Duursma, A. Minnaard, B. L. Feringa, J. Am. Chem. Soc. 2003, 125, 3700-3701;
28. c) C. A. Luchaco-Cullis, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 8192-8193; for α,β-unsaturated N-acyloxazolidinones and amides:
29. d) A. W. Hird, A. H. Hoveyda, Angew. Chem. 2003, 115, 1314-1317;
30. Angew. Chem. Int. Ed. 2003, 42, 1276-1279; for lactones:
31. e) L. Liang, L. Su, X. Li, A. S. C. Chan, Tetrahedron Lett. 2003, 44, 7217-7220;
32. f) M. Yan, Z. Y. Zhou, A. S. C. Chan, Chem. Commun. 2000, 115-116;
33. g) M. T. Reetz, A. Gosberg, D. Moulin, Tetrahedron Lett. 2002, 43, 1189-1191; for lactams:
34. h) M. Pineschi, F. Del Moro, F. Gini, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2004, 1244-1245; for malonates:
35. i) J. Schuppan, A. J. Minnaard, B. L. Feringa, Chem. Commun. 2004, 792-793;
36. j) T. Watanabe, T. F. Knopfel, E. M. Carreira, Org. Lett. 2003, 5, 4557-4558;
37. k) A. Alexakis, C. Benhaim, Tetrahedron: Asymmetry 2001, 12, 1151-1157.
38. a) M. Kitamura, T. Miki, K. Nakano, R. Noyori, Tetrahedron Lett. 1996, 37, 5141-5144;
39. b) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos, A. H. M. de Vries, Angew. Chem. 1997, 109, 2733-2736;
40. Angew. Chem. Int. Ed. Engl. 1997, 36, 2620-2623;
41. e) E. Keller, J. Maurer, R. Nassz, T. Schader, A. Meetsma, B. L. Feringa, Tetrahedron: Asymmetry 1998, 9, 2409-2413;
42. d) L. A. Arnold, R. Nassz, A. J. Minnaard, B. L. Feringa, J. Org. Chem. 2002, 67, 7244-7254.
43. R. Naasz, L. A. Arnold, M. Pineschi, E. Keller, B. L. Feringa, J. Am. Chem. Soc. 1999, 121, 1104-1105.
44. H. Mizutani, S. J. Degrado, A. H. Hoveyda, J. Am. Chem. Soc. 2002, 124, 779-781
45. X. Rathgeb, S. March, A. Alexakis, J. Org. Chem. 2006, 71, 5737-5742.
46. a) K. Oliver, A. Alexakis, Org. Lett. 2002, 4, 3835-3837;
47. b) A. Alexakis, S. March, J. Org. Chem. 2002, 67, 8753-8757.
48. K. Y. Li, A. Alexakis, Tetrahedron Lett. 2005, 46, 5823-5826.
49. K. Agapiou, D. F. Cauble, M.J. Krische, J. Am. Chem. Soc. 2004, 126, 4528-4529.
50. For a preliminary communication: K. Y. Li, A. Alexakis, Tetrahedron Lett. 2005, 46, 8019-8022.
51. K. Tissot-Croset, D. Polet, S. Gille, C. Hawner, A. Alexakis, Synthesis 2004, 15, 2586-2590.
52. a) E. Lorthiois, I. Marek, C. Meyer, J. F. Normant, Tetrahedron Lett. 1995, 36, 1263-1266;
53. b) C. Meyer, I. Marek, J. F. Normant, Tetrahedron Lett. 1996, 37, 857-860;
54. c) E. Lorthiois, I. Marek, J. F. Normant, Tetrahedron Lett. 1997, 38, 89-92;
55. d) E. Lorthiois, I. Marek, J. F. Normant, J. Org. Chem. 1998, 63, 566-574;
56. e) E. Lorthiois, I. Marek, J. F. Normant, J. Org. Chem. 1998, 63, 2442-2450;
57. f) F. Denes, F. Chemla, J. F. Normant, Eur. J. Org. Chem. 2002, 3536-3542;
58. g) F. Denes, F. Chemla, J. F. Normant, Angew. Chem. 2003, 115, 4177-4180;
59. Angew. Chem. Int. Ed. 2003, 42, 4043-4046.
60. a) M. Nakamura, T. Hatakeyama, K. Hara, E. Nakamura, J. Am. Chem. Soc. 2003, 125, 6362-6363;
61. b) M. Nakamura, T. Hatakeyama, E. Nakamura, J. Am. Chem. Soc. 2004, 126, 11820-11825.
62. J. Bentley, P. A. Nilsson, A. F. Parsons, J. Chem. Soc. Perkin Trans. 1 2002, 1461-1469.
63. I. N. Houpis, J. Lee, Tetrahedron 2000, 56, 817-846.
64. a) E. J. Enholm, K. S. Kinter, J. Org. Chem. 1995, 60, 4850-4855;
65. b) D. Bebbington, J. Bentley, P. A. Nilsson, A. F. Parsons, Tetrahedron Lett. 2000, 41, 8941-8945;
66. c) P. M. Brown, N. Käppel, P. J. Murphy, Tetrahedron Lett. 2002, 43, 8707-8710.
67. a) C. Borner, M. R. Dennis, E. Sinn, S. Woodward, Eur. J. Org. Chem. 2001, 2435-2446;
68. b) V. Garcia-Ruiz, S. Woodward, Tetrahedron: Asymmetry 2002, 13, 2177-2180.
69. J. K. Yang, D. F. Cauble, A. J. Berro, N. L. Bauld, M. J. Krische, J. Org. Chem. 2004, 69, 7979-7984.
70. L. M. Jackman, B. C. Lange, J. Org. Chem. 1983, 48, 4789-4792.
71. G. Pandey, S. Hajra, M. K. Ghorai, K. R. Kumar, J. Am. Chem. Soc. 1997, 119, 8777-8787.
72. R. R. Huddleston, D. F. Cauble, M. J. Krische, J. Org. Chem. 2003, 68, 11-14.
73. K. R. Roesch, R. C. Larock, J. Org. Chem. 2001, 66, 412-420.
74. C. Spino, J. Crawford, J. Bishop, J. Org. Chem. 1995, 60, 844-851.
75. J. Montgomery, A. V. Savchenko, Y. B. Zhao, J. Org. Chem. 1995, 60, 5699-5701.
76. P. J. Murphy, Tetrahedron 2001, 57, 7771-7784.
77. R. Suero, J. M. Gorgojo, J. M. Aurrecoechea, Tetrahedron 2002, 58, 6211-6221.
78. J. P. Marino, H. N. Nguyen, J. Org. Chem. 2002, 67, 6291-6296.