Radical cascade cyclizations and platinum(II)-catalyzed cycloisomerizations of ynamides

Tetrahedron

Volumn 62, Issue 16, 2006, Pages 3856-3871

  Marion, Frédéric ^a   Coulomb, Julien ^a   Servais, Aurore ^a   Courillon, Christine ^a   Fensterbank, Louis ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

(Tosyl) ynamides; Cycloisomerization; Heterocycles; Platinum; Radical Cascades; Radical cyclization

Indexed keywords

AMIDE; CARBOLINE DERIVATIVE; ISOINDOLE DERIVATIVE; ISOINDOLINONE DERIVATIVE; PLATINUM; PYRIDOISOINDOLONE DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; UNCLASSIFIED DRUG; YNAMIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; ISOMERIZATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33645298511     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.11.092     Document Type: Article

References (97)

1. Ficini, J. Tetrahedron 1976, 32, 1449-1486.
2. Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389-1390.
3. Wolf, V.; Kowitz, F. Ann. 1960, 638, 33-42.
4. Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1967, 6, 77-78 see also pages 767-778.
5. Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575-7606.
6. Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. Engl. 1972, 11, 917-918.
7. Brückner, D. Synlett 2000, 1402-1404.
8. Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459-466.
9. Joshi, R. V.; Xu, Z.-Q.; Ksebati, M. B.; Kessel, D.; Corbett, T. H.; Drach, J. C.; Zemlicka, J. J. Chem. Soc., Perkin Trans. 1 1994, 1089-1098.
10. Zaugg, H. E.; Swett, L. R.; Stone, G. R. J. Org. Chem. 1958, 23, 1389-1390.
11. (a) Galy, J. P.; Elguero, J.; Vincent, E. J.; Barbe, J. Synthesis 1979, 944-946.
12. (b) Mahamoud, A.; Galy, J. P.; Vincent, E. J.; Barbe, J. Synthesis 1981, 917-918.
13. (c) Katritzky, A. R.; Ramer, W. H. J. Org. Chem. 1985, 50, 852-856.
14. Hsung, R. P.; Zificsak, C. A.; Wei, L.-L.; Douglas, C. J.; Mulder, J. A.; Xiong, H. Org. Lett. 1999, 1237-1240.
15. Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 2417-2420.
16. Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1998, 37, 489-492.
17. Witulski, B.; Gößmann, M. Synlett 2000, 1793-1797.
18. Balsamo, A.; Macchia, B.; Macchia, F.; Rossello, A. Tetrahedron Lett. 1985, 26, 4141-4144.
19. (a) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368-2369.
20. (b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379-1390.
21. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
22. Schottelius, M. J.; Chen, P. Helv. Chim. Acta 1998, 81, 2341-2347.
23. Novikov, M. S.; Khlebnikov, A. F.; Kostikov, R. R. Zhurnal Organicheskoi Khimii 1991, 27, 1794-1795.
24. Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405-5418.
25. Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011-4014.
26. Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151-1154.
27. (a) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
28. (b) Witulski, B.; Stengel, T.; Fernandèz-Hernandèz, J. M. Chem. Commun. 2000, 1965-1966.
29. (c) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430.
30. (a) Rainier, J. D.; Imbroglio, J. E. J. Org. Chem. 2000, 65, 7272-7276.
31. (b) Witulski, B.; Gößmann, M. Chem. Commun. 1999, 1879-1880.
32. (c) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353-9358.
33. Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681-3684.
34. (a) Witulski, B.; Lumtscher, J.; Bergstraber, U. Synlett 2003, 708-710.
35. (b) Martínez-Esperón, M. F.; Rodríguez, D.; Castedo, L.; Saá, C. Org. Lett. 2005, 7, 2213-2216.
36. (c) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776-5777.
37. (a) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar, C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417-2420.
38. (b) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803-805.
39. Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67-70.
40. (a) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547-1550.
41. (b) Witulski, B.; Bushmann, N.; Bergstraber, U. Tetrahedron 2000, 56, 8473-8480.
42. (a) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663-2666.
43. (b) Mulder, J. A.; Hsung, R. P.; Fredrick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383-1386.
44. (a) Couty, S.; Liegault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511-2514.
45. (b) Chechik-Lankin, H.; Livshin, S.; Marek, I. Synlett 2005, 2098-2100.
46. (a) Dhimane, A.-L.; Aissa, C.; Malacria, M. Angew. Chem., Int. Ed. 2002, 41, 3284-3287.
47. (b) Fensterbank, L.; Mainetti, E.; Devin, P.; Malacria, M. Synlett 2000, 1342-1344.
48. (c) Devin, P.; Fensterbank, L.; Malacria, M. J. Org. Chem. 1998, 63, 6764-6765.
49. (d) Dhimane, A.-L.; Fensterbank, L.; Malacria, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 350-382.
50. (a) Blaszykowski, C.; Dhimane, A.-L.; Fensterbank, L.; Malacria, M. Org. Lett. 2003, 5, 1341-1344.
51. (b) Devin, P.; Fensterbank, L.; Malacria, M. Tetrahedron Lett. 1999, 40, 5511-5514.
52. (a) Russel Bowman, W.; Fletcher, A. J.; Potts, G. B. S. J. Chem. Soc., Perkin Trans. 1 2002, 2747-2762.
53. (b) Zhang, W.; Pugh, G. Tetrahedron 2003, 59, 3009-3018.
54. (c) Du, W.; Curran, D. P. Org. Lett. 2003, 5, 1765-1768.
55. (d) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404.
56. (e) Boiteau, L.; Boivin, J.; Liard, A.; Quiclet-Sire, B.; Zard, S. Z. Angew. Chem., Int. Ed. 1998, 37, 1128-1131.
57. (f) Zhou, S.; Bommezijn, S.; Murphy, J. A. Org. Lett. 2002, 4, 443-445.
58. (g) Renaud, P.; Ollivier, C.; Panchaud, P. Angew. Chem., Int. Ed. 2002, 41, 3460-3462.
59. (h) Taniguchi, T.; Iwasaki, K.; Uchiyama, M.; Tamura, O.; Ishibashi, H. Org. Lett. 2005, 7, 4389-4390.
60. For a preliminary communication, see: Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095-5097.
61. Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 905-910.
62. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
63. (b) Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
64. (a) Stork, G.; Mook, R. J. Am. Chem. Soc. 1987, 109, 2829-2831.
65. (b) Nozaki, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1987, 109, 2547-2549.
66. Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188-194.
67. Giraud, L.; Lacôte, E.; Renaud, P. Helv. Chem. Acta 1997, 80, 2148-2156.
68. Parsons, P. J.; Penverne, M.; Pinto, I. L. Synlett 1994, 721-722.
69. (a) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834.
70. (b) LLoyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215-236.
71. (c) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16.
72. (a) Chatani, N.; Kataoka, K.; Murai, S.; Furukawa, N.; Seki, Y. J. Am. Chem. Soc. 1998, 120, 9104-9105.
73. (b) Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511-10520.
74. (c) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305-8314.
75. (d) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863-11869.
76. (e) Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Chem. Eur. J. 2003, 9, 2627-2635.
77. (f) For reviews, see: Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts 2003, 16, 397-425.
78. (g) Anorbe, L.; Dominguez, G.; Pérez-Castells, J. Chem. Eur. J. 2004, 10, 4938-4943.
79. (a) Mainetti, E.; Mouriès, V.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. Angew. Chem., Int. Ed. 2002, 41, 2132-2135.
80. (b) Cadran, N.; Cariou, K.; Hervé, G.; Aubert, C.; Fensterbank, L.; Malacria, M.; Marco-Contelles, J. J. Am. Chem. Soc. 2004, 126, 3408-3409.
81. Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A. Org. Lett. 2005, 7, 1047-1050.
82. Katritzky, A. R.; Chang, H.-X.; Yang, B. Synthesis 1995, 503-504.
83. Isolation of cyclobutenes from metal catalyzed [2+2] of enynes has been described, see: (a) Pd (II): Trost, B. M.; Yanai, M.; Hoogsten, K. J. Am. Chem. Soc. 1993, 115, 5294-5295.
84. (b) Trost, B. M.; Tanoury, G. J. J. Am. Chem. Soc. 1988, 110, 1636-1638. In the latter case, the double bond is shifted to give a more stable cyclobutene product.
85. (c) Pt(II), see Ref. 44d.
86. (d) Fürstner, A.; Davies, P. W.; Gress, T. J. Am. Chem. Soc. 2005, 127, 8244-8245.
87. (e) Pt(IV): Blum, J.; Beer-Kraft, H.; Badrieh, Y. J. Org. Chem. 1985, 60, 5567-5569. In that case, the cyclobutene adduct reacts with O2.
88. (f) Ga (III): Chatani, N.; Inoue, H.; Kotsuma, T.; Murai, S. J. Am. Chem. Soc. 2002, 124, 10294-10295.
89. For a related report of instability, see: Smith, A. B., III; Cui, H. Org. Lett. 2003, 5, 587-590 and Ref. 48e.
90. (a) Strobel, M. P.; Morin, L.; Paquer, D. New J. Chem. 1980, 4, 603-608.
91. (b) Mahajan, J. R.; Ferreira, A. L.; Araújo, H. C.; Nunes, B. J. Synthesis 1976, 112-113.
92. Soriano, E.; Marco-Contelles, J. J. Org. Chem. 2005, 70, 9345-9353.
93. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1991, 113, 224-232.
94. Nieto-Oberhuber, C.; Lopez, S.; Paz Muñoz, M.; Cárdenas, D. J.; Buñuel, E.; Nevado, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2005, 44, 6146-6148.
95. The analysis of the crude cycloisomerization product from precursor 54 is consistent with the formation of an exocyclobutene intermediate.
96. Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431-436.
97. For a preliminary communication, see: Marion, F.; Coulomb, J.; Fensterbank, L.; Courillon, C.; Malacria, M. Org. Lett. 2004, 6, 1509-1511.