Some recent applications of Fischer carbenemetal complexes in organic synthesis

Journal of Organometallic Chemistry

Volumn 690, Issue 24-25, 2005, Pages 5900-5911

  Wu, Yao Ting ^a,b   Kurahashi, Takuya ^a   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Angular and linear triquinanes; Cascade reactions; Fischer carbene complexes; Steroid like molecules; Template effect; Transmetallation

Indexed keywords

CASCADE CONNECTIONS; SYNTHESIS (CHEMICAL);

ANGULAR AND LINEAR TRIQUINANES; CASCADE REACTIONS; FISCHER CARBENE COMPLEXES; STEROID-LIKE MOLECULES; TEMPLATE EFFECT; TRANSMETALLATION;

ORGANIC COMPOUNDS;

EID: 27744603938     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2005.07.082     Document Type: Article

References (73)

1. E.O. Fischer, and A. Maasböl Angew. Chem. 76 1964 645
2. Angew. Chem., Int. Ed. Engl. 3 1964 580
3. C.P. Casey, and R.L. Anderson J. Am. Chem. Soc. 96 1974 1230
4. W.D. Wulff L.S. Liebeskind Advances in Metal-Organic Chemistry vol. 1 1989 JAI Press London 209
5. Carbene complexes in general are isolobal with the corresponding organic carbonyl compounds: R. Hoffmann Angew. Chem. 94 1982 725
6. Angew. Chem., Int. Ed. Engl. 21 1982 711
7. For recent reviews on Fischer carbene complexes in organic synthesis, see: M. Gómez-Gallego, M.J. Mancheño, and M.A. Sierra Acc. Chem. Res. 38 2005 44
8. J. Barluenga, M.A. Fernández-RodrIíguez, and E. Aguilar J. Organomet. Chem. 690 2005
9. Y.-T. Wu, and A. de Meijere K.H. Dötz Top. Organomet. Chem 13 2004 21
10. J. Barluenga, F. RodrIÍguez, F.J. Frañanás, and J. Flrenz K.H. Dötz Top. Organomet. Chem. 13 2004 59
11. A. Minatti, and K.H. Dötz K.H. Dötz Top. Organomet. Chem. 13 2004 123
12. L.S. Hegedus K.H. Dötz Top. Organomet. Chem. 13 2004
13. A. de Meijere, H. Schirmer, and M. Duetsch Angew. Chem. 112 2000 4124
14. Angew. Chem., Int. Ed. 39 2000 3964
15. R. Aumann Eur. J. Org. Chem. 2000 17
16. J. Barluenga, and F.J. Frañanás Tetrahedron 56 2000 4597
17. J.W. Herndon Tetrahedron 56 2000 1257
18. M.A. Sierra Chem. Rev. 100 2000 3591
19. F. Zaragoza Dörwald Metal Carbenes in Organic Synthesis 1999 Wiley-VCH Weinheim
20. J.W. Herndon Coord. Chem. Rev. 181 1999 177
21. F. Stein, M. Duetsch, E. Pohl, R. Herbst-Irmer, and A. de Meijere Organometallics 12 1993 2556
22. M. Duetsch, F. Stein, R. Lackmann, E. Pohl, R. Herbst-Irmer, and A. de Meijere Chem. Ber. 125 1992 2051
23. Y.-T. Wu, B. Flynn, H. Schirmer, F. Funke, S. Müller, T. Labahn, M. Nötzel, and A. de Meijere Eur. J. Org. Chem. 2004 724
24. K.H. Dötz, I. Pruskil, and J. Mühlemeier Chem. Ber. 115 1982 1278
25. K.H. Dötz, and W. Kuhn Angew. Chem. 95 1983 750
26. Angew. Chem., Int. Ed. Engl. 22 1983 732 for a recent review, see also [5e]
27. For a recent application of Dötz reaction to prepare trisquinone, see: M.X.-W. Jiang, M. Rawat, and W.D. Wulff J. Am. Chem. Soc. 126 2004 5970
28. For the synthesis of calixarenes, see: V. Gopalsamuthiram, and W.D. Wulff J. Am. Chem. Soc. 126 2004 13936
29. Preliminary communication see: B.L. Flynn, F.J. Funke, C.C. Silveira, and A. de Meijere Synlett 1995 1007
30. M. Duetsch, R. Lackmann, F. Stein, and A. de Meijere Synlett 1991 324
31. B. Flynn, and A. de Meijere J. Org. Chem. 64 1999 400
32. B. Flynn, H. Schirmer, M. Duetsch, and A. de Meijere J. Org. Chem. 66 2001 1747
33. J. Milic, H. Schirmer, B. Flynn, M. Noltemeyer, and A. de Meijere Synlett 2002 875
34. H. Schirmer, F.J. Funke, S. Müller, M. Noltemeyer, B. Flynn, and A. de Meijere Eur. J. Org. Chem. 1999 2025
35. Y.-T. Wu, D. Vidovic, J. Magull, and A. de Meijere Eur. J. Org. Chem. 2005 1625
36. Y. Zhang, and J.W. Herndon Org. Lett. 5 2003 2043
37. J.W. Herndon, and H. Wang J. Org. Chem. 63 1998 4564
38. Y.-T. Wu, M. Noltemeyer, and A. de Meijere Eur. J. Org. Chem. 2005 2802
39. S.S. Elmorsy, A. Pelter, and K. Smith Tetrahedron Lett. 32 1991 4175
40. S. Ranganathan, K.M. Muraleedharan, P. Bharadwaj, and K.P. Madhusudanan Chem. Commun. 1998 2239
41. N.O. Mahmoodi, and N. Hajati J. Chin. Chem. Soc. 49 2002 91
42. H. Shirai, N. Amano, Y. Hashimoto, E. Fukui, Y. Ishii, and M. Ogawa J. Org. Chem. 56 1991 2253
43. M.M. Boorum, and L.T. Scott D. Astruc Modern Arene Chemistry 2002 Wiley-VCH Weinheim 20
44. R. Aumann, I. Göttker-Schnetmann, R. Fröhlich, and O. Meyer Eur. J. Org. Chem. 1999 2545
45. I. Göttker-Schnetmann, and R. Aumann Organometallics 20 2001 346
46. J. Barluenga, R. Vicente, L.A. Lpez, E. Rubio, M. Tomás, and C. Álvarez-Rúa J. Am. Chem. Soc. 126 2004 470
47. Preliminary communication see: F. Stein, M. Duetsch, R. Lackmann, M. Noltemeyer, and A. de Meijere Angew. Chem. 103 1991 1669
48. Angew. Chem., Int. Ed. Engl. 30 1991 1658
49. A. de Meijere, H. Schirmer, F. Stein, F. Funke, M. Duetsch, Y.-T. Wu, M. Noltemeyer, T. Belgardt, and B. Knieriem Chem. Eur. J. 11 2005 4132
50. J. Barluenga, P. Barrio, L.A. Lpez, M. Tomás, S. CarcIÍa-Granda, and C. Álvarez-Rúa Angew. Chem. 115 2003 3116
51. Angew. Chem., Int. Ed. 42 2003 3008
52. H. Schirmer, M. Duetsch, F. Stein, T. Labahn, B. Knieriem, and A. de Meijere Angew. Chem. 111 1999 1369
53. Angew. Chem., Int. Ed. 38 1999 1285
54. H. Schirmer, B.L. Flynn, and A. de Meijere Tetrahedron 56 2000 4977
55. H. Rudler, A. Parlier, M. del Pilar Peregrina, and J. Vaissermann Organometallics 24 2005 1
56. H. Rudler, A. Parlier, V. Certal, G. Lastennet, M. Audouin, and J. Vaissermann Eur. J. Org. Chem. 2004 2471
57. K.H. Dötz, T. Schäfer, F. Kroll, and K. Harms Angew. Chem., Int. Ed. Engl. 31 1992 1236
58. A. Parlier, H. Rudler, N. Platzer, M. Fontanille, and A. Soum J. Organomet. Chem. 287 1995 C8
59. P.F. Korkowski, T.R. Hoye, and D.B. Rydberg J. Am. Chem. Soc. 110 1988 2676
60. J.W. Herndon, and S.U. Tumer J. Am. Chem. Soc. 110 1988 3334
61. J.W. Herndon, S.U. Tumer, L.A. McMullen, J.J. Matasi, and W.F.K. Schnatter L.S. Liebeskind Advances in Metal-Organic Chemistry vol. 3 1994 JAI Press London 51
62. J.W. Herndon, S.U. Tumer, and W.F.K. Schnatter J. Am. Chem. Soc. 110 1988 3334
63. J.W. Herndon, and S.U. Tumer Tetrahedron Lett. 30 1989 295
64. C.-C. Hwu, F.-C. Wang, M.-C.P. Yeh, and J.-H. Sheu J. Organomet. Chem. 474 1994 123
65. J. Barluenga, F. Aznar, and A. Martín Organometallics 14 1995 1429
66. T. Kurahashi, Y.-T. Wu, K. Meindl, S. Rühl, and A. de Meijere Synlett 2005 805
67. N. Krause A.S.K. Hashmi Modern Allene Chemistry 2004 Wiley-VCH Weinheim
68. H.A. Wegner, A. de Meijere, and P.A. Wender J. Am. Chem. Soc. 127 2005 6530
69. R. Aumann, and J. Uphoff Angew. Chem. 99 1987 361
70. Angew. Chem., Int. Ed. Engl. 26 1987 357
71. J. Barluenga, R. Vicente, P. Barrio, L.A. Lpez, and M. Tomás J. Am. Chem. Soc. 126 2004 5974
72. J. Tsuji Transition Metal Reagents and Catalysts 2000 Wiley Chichester p. 169
73. J. Barluenga, R. Vicente, P. Barrio, L.A. Lpez, M. Tomás, and J. Borge J. Am. Chem. Soc. 126 2004 14354