Alkoxy- and hydroxycyclization of enynes catalyzed by Pd(II) and Pt(II) catalysts

Pure and Applied Chemistry

Volumn 78, Issue 2, 2006, Pages 397-407

  Michelet, Véronique ^a   Charruault, Lise ^a   Gladiali, Serafino ^b   Genêt, Jean Pierre ^a  

^a PSL RESEARCH UNIVERSITY   (France)

^b UNIVERSITY OF SASSARI   (Italy)

Author keywords

Asymmetric catalysis; Atom economy; Cycloisomerization; Palladium; Platinum

Indexed keywords

EID: 33644509189     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200678020397     Document Type: Conference Paper

References (85)

1. For recent reviews on atom economy processes, see: (a) B. M. Trost. Acc. Chem. Res. 35, 695 (2002);
2. (b) P. N. Anastas and M. M. Kirchhoff. Acc. Chem. Res. 35, 686 (2002);
3. (c) B. M. Trost, D. F. Toste, A. B. Pinkerton. Chem. Rev. 101, 2067 (2001);
4. (d) B. M. Trost and M. J. Krische. Synlett 1 (1998);
5. (e) B. M. Trost. Science 254, 1471 (1991).
6. For reviews on tandem reactions, see: (a) D. E. Fogg and E. N. dos Santos. Coord. Chem. Rev. 248, 2365 (2004);
7. (b) L. F. Tietze and F. Haunert. In Stimulating Concepts in Chemistry, F. Vögtle, J. F. Sdtoddart, M. Shibasaki, (Eds.), pp. 39-64, Wiley-VCH, Weinheim (2000);
8. (c) G. Poli, G. Giambastiani, A. Heumann. Tetrahedron 56, 5959 (2000);
9. (d) L. F. Tietze. Chem. Rev. 96, 115 (1996);
10. (e) S. E. Denmark and A. Thorarensen. Chem. Rev. 96, 137 (1996);
11. (f) J. D. Winkler. Chem. Rev. 96, 167 (1996);
12. (g) M. Malacria. Chem. Rev. 96, 289 (1996).
13. For representative examples, see: (a) F. Alonso, I. P. Beletskaya, M. Yus. Chem. Rev. 104, 3079 (2004);
14. (b) I. Nakamura and Y. Yamamoto. Chem. Rev. 104, 2127 (2004);
15. (c) M. Beller, J. Seayad, A. Tillack, H. Jiao. Angew. Chem., Int. Ed. 43, 3368 (2004).
16. For representative examples, see: (a) G. Zeni and R. C. Larock. Chem. Rev. 104, 2285 (2004);
17. (b) G. Balme, N. Monteiro, D. Bouyssi. In Handbook of Organopalladium Chemistry for Organic Synthesis, E. I. Negishi (Ed.), pp. 2245-2265, John Wiley, New York (2002);
18. (c) T. Hosokawa and S.-I. Murahashi. In Handbook of Organopalladium Chemistry for Organic Synthesis, E. I. Negishi (Ed.), pp. 2169-2192, John Wiley, New York (2002);
19. (d) J. Tsuji. Palladium Reagents and Catalysis, Wiley-VCH, New York (1996);
20. (e) T. Hosokawa and S.-I. Murahashi. Acc. Chem. Res. 23, 49 (1990);
21. (f) K. Utimoto. Pure Appl. Chem. 55, 1845 (1983).
22. For recent reviews, see: (a) C. Aubert, O. Buisine, M. Malacria. Chem. Rev. 102, 813 (2002);
23. (b) M. Méndez, V. Mamane, A. Fürstner. Chemtracts-Org. Chem. 16, 397 (2003);
24. (c) G. C. Lloyd-Jones. Org. Biomol. Chem. 1, 215 (2003);
25. (d) A. M. Echavarren and C. Nevado. Chem. Soc. Rev. 33, 431 (2004);
26. (e) C. Bruneau. Angew. Chem., Int. Ed. 44, 2328 (2004);
27. (f) L. Anorbe, G. Dominguez, J. Perez-Castelles. Chem. Eur. J. 10, 4938 (2004);
28. (g) I. J. S. Fairlamb. Angew. Chem., Int. Ed. 43, 1048 (2004).
29. (a) E. G. Kuntz. CHEMTECH 570 (1987);
30. (b) B. Cornils and E. G. Kuntz. J. Organomet. Chem. 502, 177 (1995);
31. (c) V. Michelet, M. Savignac, J.-P. Genêt. In Electronic Encyclopedia of Reagents for Organic Synthesis, L. Paquette, P. Fuchs, D. Crich, P. Wipf (Eds.), John Wiley (2004).
32. J.-C. Galland, M. Savignac, J.-P. Genêt. Tetrahedron Lett. 38, 8695 (1997).
33. (a) C. Nevado, L. Charruault, V. Michelet, C. Nieto-Oberhuber, M. P. Munoz, M. Méndez, M.-N. Rager, J.-P. Genêt, A. M. Echavarren. Eur. J. Org. Chem. 706 (2003);
34. (b) C. Nevado, D. J. Cárdenas, A. M. Echavarren. Chem. Eur. J. 9, 2627 (2003);
35. (c) B. Martin-Matute, C. Nevado, D. J. Cárdenas, A. M. Echavarren. J. Am. Chem. Soc. 125, 5757 (2003);
36. (d) M. Méndez, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren. J. Am. Chem. Soc. 123, 10511 (2001);
37. (e) M. Méndez, M. P. Muñoz, A. M. Echavarren. J. Am. Chem. Soc. 122, 11549 (2000).
38. (a) L. Charruault, V. Michelet, J.-P. Genêt. Tetrahedron Lett. 43, 4757 (2002);
39. (b) J.-C. Galland, S. Diaz, M. Savignac, J.-P. Genêt. Tetrahedron 57, 5137 (2001).
40. L. Charruault, V. Michelet, R. Taras, S. Gladiali, J.-P. Genêt. Chem. Commun. 850 (2004).
41. L. Charruault, V. Michelet, J.-P. Genêt. Unpublished results.
42. A. Miyashita, A. Yasuda, R. Noyori. J. Am. Chem. Soc. 102, 7932 (1980).
43. (a) R. Schmid, J. Foricher, M. Cereghetti, P. Schönholzer. Helv. Chim. Acta 74, 370 (1991);
44. (b) R. Schmid, A. E. Broger, M. Cereghetti, J. Foricher, M. Lalonde, R. K. Müller, M. Scalone, G. Schoettel, U. Zutter. Pure Appl. Chem. 68, 131 (1996).
45. (a) T. P. Dang and H. B. Kagan. J. Chem. Soc., Chem. Commun. 481 (1971);
46. (b) T. P. Dang and H. B. Kagan. J. Am. Chem. Soc. 94, 1612 (1972).
47. (a) W. S. Knowles and M. J. Sabacky. J. Chem. Soc., Chem. Commun. 1445 (1968);
48. (b) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff. J. Am. Chem. Soc. 97, 2567 (1975).
49. (a) A. Marinetti, F. Labrue, J.-P. Genêt. Synlett 1975 (1999);
50. (b) U. Berens, M. J. Burk, A. Gerlach, W. Hems. Angew. Chem., Int. Ed. 39, 1981-1984 (2000).
51. M. J. Burk. J. Am. Chem. Soc. 113, 8518 (1991).
52. (a) S. Gladiali, A. Dore, D. Fabbri, O. De Lucchi, M. Manassero. Tetrahedron: Asymmetry 5, 511 (1994);
53. (b) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller. J. Organomet. Chem. 675, 91 (2003);
54. (c) K. Junge, G. Oehme, A. Monsees, T. Riermeier, U. Dingerdissen, M. Beller. Tetrahedron Lett. 43, 4977 (2002).
55. (a) A. Togni. Angew. Chem., Int. Ed. Engl. 35, 1475 (1996);
56. (b) A. Togni, C. Breutel, F. Schnyder, H. Landert, A. Tijani. J. Am. Chem. Soc. 116, 4062 (1994).
57. (a) F. Robin, F. Mercier, L. Ricard, F. Mathey, M. Spagnol. Chem. Eur. J. 3, 1365 (1997);
58. (b) F. Mathey, F. Mercier, F. Robin, L. Ricard. J. Organomet. Chem. 557, 117 (1998).
59. (a) A. K. Ghosh and H. Matsuda. Org. Lett. 1, 2157 (1999);
60. (b) A. Fürstner, D. Voigtländer, W. Schrader, D. Giebel, M. T. Reetz. Org. Lett. 3, 417 (2001);
61. (c) N. M. Brunkan and M. R. Gagné. Organometallics 21, 1576 (2002);
62. For a recent review, see: G. Strukul. Top. Catal. 19, 33 (2002).
63. (a) J.-C. Fiaud and A. Horeau. Stereochemistry, Vol. 3, H. B. Kagan (Ed.), pp. 51-94, George Thieme, Stuttgart (1977);
64. (b) B. Wu and H. S. Mosher. J. Org. Chem. 51, 1904 (1986);
65. (c) B. M. Trost, J. L. Belletire, S. Godelski, P. G. McDougal, J. M. Balkovec. J. Org. Chem. 51, 2370 (1986);
66. (d) I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa. J. Am. Chem. Soc. 113, 4092 (1991).
67. (a) M. P. Muñoz, J. Adrio, J. C. Carretero, A. M. Echavarren. Organometallics 24, 1293 (2005);
68. (b) C. Nieto-Oberhuber, S. Lopez, A. M. Echavarren. J. Am. Chem. Soc. 127, 6178 (2005);
69. (c) C. Nieto-Oberhuber, M. P. Muñoz, C. Nevado, D. J. Cárdenas, A. M. Echavarren. Angew. Chem., Int. Ed. 43, 2402 (2004).
70. E. Genin, A. Escalle, V. Michelet, J.-P. Genêt. Unpublished results.
71. For representative examples and seminal references, see: (a) A. S. K. Hashmi. Gold Bull. 37, 51 (2004);
72. (b) A. Arcadi and S. Di Giuseppe. Curr. Org. Chem. 8, 795 (2004);
73. (c) A. S. K. Hashmi, L. Schwarz, J.-H. Choi, T. M. Frost. Angew. Chem., Int. Ed. 39, 2285 (2000);
74. (d) C.-G. Yang and C. He. J. Am. Chem. Soc. 127, 6966 (2005);
75. (e) M. Alfonsi, A. Arcadi, M. Aschi, G. Bianchi, F. Marinelli. J. Org. Chem. 70, 2265 (2005);
76. (f) B. D. Sherry and F. D. Toste. J. Am. Chem. Soc. 126, 15978 (2004);
77. (g) G. Dyker. Angew. Chem., Int. Ed. 39, 4237 (2000);
78. (h) L. Zhang and S. A. Kozmin. J. Am. Chem. Soc. 126, 11806 (2004);
79. (i) S. T. Staben, J. J. Kennedy-Smith, F. D. Toste. Angew. Chem., Int. Ed. 43, 5345 (2005);
80. (j) J. P. Markharn, S. T. S. Staben, F. D. Toste. J. Am. Chem. Soc. 127, 9708 (2005);
81. (k) J. J. Kennedy-Smith, S. T. Staben, F. D. Toste. J. Am. Chem. Soc. 126, 4526 (2004);
82. (l) X. Shi, D. J. Gorin, F. D. Toste. J. Am. Chem. Soc. 127, 5802 (2005);
83. (m) D. J. Gorin, N. R. Davis, F. D. Toste. J. Am. Chem. Soc. 127 11260 (2005).
84. E. Genin, S. Antoniotti, V. Michelet, J.-P. Genêt. Angew. Chem., Int. Ed. 44, 4949 (2005).
85. S. Antoniotti, E. Genin, V. Michelet, J.-P. Genêt. J. Am. Chem. Soc. 127, 9976 (2005).