Straightforward synthesis of di-, tri- and tetracyclic lactams via catalytic Pauson-Khand and Alder-Ene reactions of MCR products

Tetrahedron

Volumn 61, Issue 48, 2005, Pages 11345-11354

  Strübing, Dirk ^a   Neumann, Helfried ^a   Hübner, Sandra ^a   Klaus, Stefan ^a   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Alder ene reactions; Enynes; Multicomponent reactions; Pauson Khand reactions

Indexed keywords

ALDEHYDE; AMIDE; LACTAM;

ARTICLE; CATALYSIS; PAUSON KHAND REACTION; PRIORITY JOURNAL; QUANTUM YIELD; SYNTHESIS;

BETULACEAE;

EID: 27444442356     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.098     Document Type: Article

References (80)

1. A. Dömling, and I. Ugi Angew. Chem., Int. Ed. 39 2000 3168
2. H. Bienaymé, C. Hulme, G. Oddon, and P. Schmitt Chem. Eur. J. 6 2000 3321
3. L.F. Tietze Chem. Rev. 96 1996 115
4. L.F. Tietze, and F. Haunert M. Shibasaki J.F. Stoddart F. Vögtle Stimulating Concepts in Chemistry 2000 Wiley-VCH Weinheim 39
5. L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304
6. G.H. Posner Chem. Rev. 86 1986 831
7. R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, and T.A. Keating Acc. Chem. Res. 29 1996 123
8. For selected recent examples see: (a) D.J. Vugts, H. Jansen, R.F. Schmitz, F.J.J. de Kanter, and R.V.A. Orru Chem. Commun. 2003 2594
9. R. Frey, S.G. Galbraith, S. Guelfi, C. Lamberth, and M. Zeller Synlett 2003 1536
10. C. Hulme, and V. Gore Curr. Med. Chem. 10 2003 51
11. G. Dyker, K. Breitenstein, and G. Henkel Tetrahedron: Asymmetry 13 2002 1929
12. R. Gamez-Montano, E. Gonzalez-Zamora, P. Potier, and J.P. Zhu Tetrahedron 58 2002 6351
13. R. Zimmer, A. Ziemer, M. Gruner, I. Brudgam, H. Hartl, and H.U. Reissig Synthesis 2001 1649
14. B. Beck, S. Hess, and A. Dömling Bioorg. Med. Chem. Lett. 10 2000 1701
15. S. Heck, and A. Dömling Synlett 2000 424
16. A. de Meijere, and S. Brase J. Organomet. Chem. 576 1999 88
17. A.M. Seayad, M. Ahmed, H. Klein, R. Jackstell, T. Gross, and M. Beller Science 297 2002 1676
18. M. Ahmed, A.M. Seayad, R. Jackstell, and M. Beller J. Am. Chem. Soc. 125 2003 10311
19. A. Moballigh, R. Jackstell, and M. Beller Tetrahedron Lett. 45 2004 869
20. B. Zimmermann, J. Herwig, and M. Beller Angew. Chem., Int. Ed. 38 1999 2372
21. M. Beller, and M. Eckert Angew. Chem., Int. Ed. 39 2000 1010
22. M. Beller, M. Eckert, H. Geissler, B. Napierski, H.-P. Rebenstock, and E.W. Holla Chem. Eur. J. 4 1998 935
23. M. Beller, M. Eckert, F. Vollmüller, S. Bogdanovic, and H. Geissler Angew. Chem., Int. Ed. 36 1997 1494
24. M. Beller, M. Eckert, W.A. Moradi, and H. Neumann Angew. Chem., Int. Ed. 38 1999 1454
25. D. Gördes, H. Neumann, A. Jacobi von Wangelin, C. Fischer, K. Drauz, H.-P. Krimmer, and M. Beller Adv. Synth. Catal. 345 2003 510
26. D. Gördes, A. Jacobi von Wangelin, S. Klaus, H. Neumann, D. Strübing, S. Hübner, H. Jiao, W. Baumann, and M. Beller Org. Biomol. Chem. 2 2004 845
27. H. Neumann, A. Jacobi von Wangelin, D. Gördes, A. Spannenberg, and M. Beller J. Am. Chem. Soc. 123 2001 8398
28. A. Jacobi von Wangelin, H. Neumann, D. Gördes, A. Spannenberg, and M. Beller Org. Lett. 3 2001 2895
29. H. Neumann, A. Jacobi von Wangelin, D. Gördes, A. Spannenberg, W. Baumann, and M. Beller Tetrahedron 58 2002 2381
30. D. Strübing, H. Neumann, A. Jacobi von Wangelin, D. Gördes, S. Klaus, M. Beller, P. Braiuca, C. Ebert, L. Gardossi, and U. Kragl Tetrahedron 60 2004 683
31. H. Neumann, A. Jacobi von Wangelin, S. Klaus, D. Strübing, D. Gördes, and M. Beller Angew. Chem., Int. Ed. 42 2003 4503
32. H. Neumann, S. Klaus, M. Klawonn, D. Strübing, S. Hübner, D. Gördes, A. Jacobi von Wangelin, and M. Beller Z. Naturforsch. Teil B 59 2004 431
33. D. Strübing, A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Hübner, S. Klaus, A. Spannenberg, and M. Beller Eur. J. Org. Chem. 2005 107
34. Strübing, D.; Kirschner, A.; Neumann, H.; Hübner, S.; Klaus, S.; Bornscheuer, U. T.; Beller, M. Chem. Eur. J. 2005, 11, 4210.
35. D. Strübing, H. Neumann, A. Jacobi von Wangelin, D. Gördes, S. Klaus, M. Beller, P. Braiuca, C. Ebert, L. Gardossi, and U. Kragl Tetrahedron 60 2004 683
36. A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Klaus, H. Jiao, A. Spannenberg, T. Krüger, C. Wendler, K. Thurow, N. Stoll, and M. Beller Chem. Eur. J. 9 2003 2273
37. Jacobi von Wangelin, A.; Neumann, H.; Gördes, D.; Hübner, S.; Wendler, C.; Klaus, S.; Strübing, D.; Spannenberg,V; Jiao, H.; El Firdoussi, L.; Thurow, K.; Stoll, N.; Beller, M. Synthesis 2005, 12, 2029.
38. Strübing, D.; Neumann, H.; Klaus, S.; Hübner, S.; Beller, M. Tetrahedron 2005, 61, see doi: 10.1016/j.tet.2005.09.097.
39. A.F. Parsons Tetrahedron 52 1996 4149
40. S.F. Martin, and W. Li J. Org. Chem. 54 1989 265
41. S.F. Martin, and W. Li J. Org. Chem. 56 1991 642
42. F. Khuong-Huu, X. Monseur, G. Ratle, G. Lucaks, and R. Goutarel Tetrahedron Lett. 14 1973 1757
43. M.E. Garst, L.J. Dolby, S. Esfandiari, N.A. Fedoruk, N.C. Chamberlain, and A.A. Avey J. Org. Chem. 65 2000 7098
44. I.U. Khand, G.R. Knox, P.L. Pauson, W.E. Watts, and M.I. Foreman J. Chem. Soc., Perkin Trans. 1 1973 977
45. For selected reviews see: (a) N.E. Schore Chem. Rev. 88 1988 1081
46. N.E. Schore Org. React. 40 1991 1
47. N.E. Schore L.S. Hegedus Comprehensive organometallic chemistry II Vol. 12 1995 Pergamon Oxford 703
48. O. Geis, and H.G. Schmalz Angew. Chem., Int. Ed. 37 1998 911
49. S.T. Ingate, and J. Marco-Contelles Org. Prep. Proced. Int. 30 1988 121
50. K.M. Brummond, and J.L. Kent Tetrahedron 56 2000 3263
51. S.E. Gibson (née Thomas), and A. Stevenazzi Angew. Chem., Int. Ed. 42 2003 1800
52. D. Strübing, and M. Beller M. Beller C. Bolm Transition Metals for Organic Synthesis 2004 Wiley-VCH Weinheim 619
53. M. Malaria, C. Aubert, and D.L. Renaud Science of Synthesis 1 2002 439
54. V. Rautenstrauch, P. Megard, J. Conesa, and W. Kuster Angew. Chem., Int. Ed. Engl. 29 1990 1413
55. N. Jeong, S.H. Hwang, Y. Lee, and Y.K. Chung J. Am. Chem. Soc. 116 1994 3159
56. S.H. Hwang, Y.W. Lee, J.S. Lim, and N. Jeong J. Am. Chem. Soc. 119 1997 10549
57. T. Rajesh, and M. Periasamy Tetrahedron Lett. 40 1999 817
58. N.Y. Lee, and Y.K. Chung Tetrahedron Lett. 37 1996 3145
59. T. Sugihara, and M. Yamaguchi J. Am. Chem. Soc. 120 1998 10782
60. M. Hayashi, Y. Hashimoto, Y. Yamamoto, J. Usuki, and K. Saigo Angew. Chem., Int. Ed. 39 2000 631
61. S.U. Son, S.I. Lee, and Y.K. Chung Angew. Chem., Int. Ed. 39 2000 4158
62. T. Morimoto, N. Chatani, Y. Fukomoto, and S. Murai J. Org. Chem. 62 1997 3762
63. T. Kondo, N. Suzuki, T. Okada, and T. Mitsudo J. Am. Chem. Soc. 119 1997 6187
64. Y. Koga, T. Kobayashi, and K. Narasaka Chem. Lett. 1998 249
65. S. Lee, B.K. Sung, Sung, and N. Jeong Organometallics 17 1998 3642
66. T. Morimoto, K. Fuji, K. Tsutsumi, and K. Kakiuchi J. Am. Chem. Soc. 124 2002 3806
67. T. Shibata, N. Toshida, and K. Takagi J. Org. Chem. 67 2002 7446
68. K. Fuji, T. Morimoto, K. Tsutsumi, and K. Kakiuchi Angew. Chem. 115 2003 2511
69. Angew. Chem., Int. Ed. 42 2003 2409
70. T. Shibata, and K. Takagi J. Am. Chem. Soc. 122 2000 9852
71. For synthesis of unprotected enyne reaction precursors see: Strübing, D.; Neumann, H.; Klaus, S.; Hübner, S.; Beller, M., Tetrahedron 2005, 61, see doi: 10.1016/j.tet.2005.09.097.
72. A. Lei, J.P. Waldkirch, M. He, and X. Zhang Angew. Chem., Int. Ed. 41 2002 4526
73. For recent reviews see: (a) C. Aubert, O. Buisine, and M. Malacria Chem. Rev. 102 2002 813
74. B.M. Trost, and M.J. Krische Synlett 1998 1
75. B.M. Trost Chem. Eur. J. 4 1998 2405
76. I. Ojima, M. Tzamarioudaki, Z. Li, and R.J. Donovan Chem. Rev. 96 1996 653
77. B.M. Trost Acc. Chem. Res. 23 1990 34
78. A. Lei, J.P. Waldkirch, M. He, and X. Zhang Angew. Chem. 114 2002 4708
79. X. Xie, X. Lu, Y. Liu, and W. Xu J. Org. Chem. 66 2001 6545
80. B.M. Trost, and C. Pedregal J. Am. Chem. Soc. 114 1992 7292