Iodocarbocyclization reaction of β-ketoesters and alkynes

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2823-2826

  Barluenga, José ^a   Palomas, David ^a   Rubio, Eduardo ^a   González, José M ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34547196840     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0710459     Document Type: Article

References (64)

1. (a) Endo, K.; Hatakeyama, T.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2007, 129, 5264-5271.
2. (b) Kuninobu, Y.; Kawata, A.; Takai, K. Org. Lett. 2005, 7, 4823-4825.
3. (c) Nakamura, M.; Endo, K.; Nakamura, E. Org. Lett. 2005, 7, 3279-3281.
4. (d) Nakamura, M.; Endo, K.; Nakamura J. Am. Chem. Soc. 2003, 125, 13002-13003. For a related transformation, see also:
5. (e) Nishimura, Y.; Ameniya, R.; Yamaguchi, M. Tetrahedron Lett. 2006, 47, 1839-1843.
6. (a) Nakamura, M.; Fujimoto, T.; Endo, K.; Nakamura, E. Org. Lett. 2004, 6, 4837-4840.
7. (b) Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015-2017.
8. (c) Ameniya, R.; Fujii, A.; Arisawa, M.; Yamaguchi, M. J. Organomet. Chem. 2003, 686, 94-100.
9. (d) Arisawa, M.; Ameniya, R.; Yamaguchi, M. Org. Lett. 2002, 4, 2209-2211.
10. (e) Miura, K.; Saito, H.; Fujisawa, N.; Wang, D.; Nishikori, H.; Hosomi, A. Org. Lett. 2001, 3, 4055-4057.
11. (f) Yamaguchi, M.; Hayashi, A.; Hirama, M. J. Am. Chem. Soc. 1993, 115, 3362-3363.
12. (a) Li, Y.; Lu, Z.; Alper, H. Org. Lett. 2007, 9, 1647-1649.
13. (b) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2006, 128, 11368-11369.
14. (c) Ochiai, M.; Ito, T.; Takaoka, Y.; Masaki, Y.; Kunishima, M.; Tani, S.; Nagao, Y. J. Chem. Soc., Chem. Commun. 1990, 118-119.
15. (d) Ochia, M.; Kunishima, M.; Nagao, Y.; Fuji, K.; Shiro, M.; Fujita, E. J. Am. Chem. Soc. 1986, 108, 8281-8283.
16. Conia, J. M.; Le Perchec, P. Synthesis 1975, 1-19.
17. (a) Pérez-Hernández, N.; Febles, M.; Pérez, C.; Pérez, R.; Rodríguez, M. L.; Foces-Foces, C.; Martín, J. D. J. Org. Chem. 2006, 71, 1139-1151.
18. (b) Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486-16487.
19. (c) Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168-17169.
20. (d) Gao, Q.; Zheng. B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185-2187.
21. (e) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527.
22. (f) Kitagawa, O.; Fujiwara, H.; Suzuki, T.; Taguchi, T.; Shiro, M. J. Org. Chem. 2000, 65, 6819-6825.
23. (g) Renaud, J.-L.; Aubert, C.; Malacria, M. Tetrahedron 1999, 55, 5113-5128.
24. (h) Bouyssi, D.; Monteiro, N.; Balme, G. Tetrahedron Lett. 1999, 40, 1297-1300.
25. (i) Cruciani, P.; Stammler, R.; Aubert, C.; Malacria, M. J. Org. Chem. 1996, 61, 2699-2708.
26. (j) Boaventura, M. A.; Drouin, J.; Conia, J. M. Synthesis 1983, 801-804.
27. (a) Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350-5352.
28. (b) McDonald, F. E.; Olson, T. C. Tetrahedron Lett. 1997, 38, 7691-7692.
29. Iwasaba, N.; Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Lee, P. H. Org. Lett. 2002, 4, 4463-4466.
30. (a) Li, Y.; Yu, Z.; Alper, H. Org. Lett. 2007, 9, 1647-1649.
31. (b) Guo, L.-N.; Duan, X.-H.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2007, 72, 1538-1540.
32. (c) Zhang, D.; Liu, Z.; Yum, E.; Larock, R. C. J. Org. Chem. 2007, 72, 251-262.
33. (d) Duan, X.-H.; Guo, L.-N.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2006, 8, 3053-3056.
34. (e) Guo, L.-N.; Duan, X.-H.; Bi, H.-P.; Liu, X.-Y.; Liang, Y.-M. J. Org. Chem. 2006, 71, 3325-3327.
35. Zhang, D.; Yum, E. K.; Liu, Z.; Larock, R. C. Org. Lett. 2005, 7, 4963-4966.
36. Kitagawa, O.; Inoue, T.; Hirano, K.; Taguchi, T. J. Org. Chem. 1993, 58, 3106-3112.
37. Related cyclizations were described for N-alkyl-N- propargyl-β-ketoamides using alternative conditions: (a) Cossy, J.; Thellend, A. Tetrahedron Lett. 1990, 31, 1427-1428. Some examples of related 5-exodig radical cyclizations by atom-transfer reactions of 2-iodo-6-alkynyl esters have been reported:
38. (c) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140-3157.
39. (a) Kitagawa, O.; Suzuki, T.; Inoue, T.; Taguchi, T. Tetrahedron Lett. 1998, 39, 7357-730.
40. (b) Kitagawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y.; Taguchi, T. J. Org. Chem. 1998, 63, 9470-9475. For an account on their work on iodocarbocyclization and iodoaminocyclization reactions see:
41. (c) Kitagawa, O.; Taguchi, T. Synlett 1999, 1191-1199.
42. Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y.-M. Org. Lett. 2007, 9, 397-400.
43. Recent work: (a) Barluenga, J.; Vázquez-Villa, H.; Merino, I.; Ballesteros, A.; González, J. M. Chem. Eur. J. 2006, 12, 5790-5805.
44. (b) Barluenga, J.; Trincado, M.; Rubio, E.; González, J. M. Angew. Chem., Int. Ed. 2006, 45, 3140-3143.
45. Representative recent work: Worlikar, S. A.; Kesharwani, T.; Yao, T.; Larock, R. C. J. Org. Chem. 2007, 72, 1347-1350.
46. (b) Amjad, M.; Knight, D. W. Tetrahedron Lett. 2006, 47, 2825-2828.
47. (c) Zhou, C.; Dubrovsky, A. V.; Larock, R. C. J. Org. Chem. 2006, 71, 1626-1632.
48. (d) Hessian, K. O.; Flynn, B. L. Org. Lett. 2006, 8, 243-246.
49. Recent iodination reactions with ring elaboration: (a) Foot, O. F.; Knight, D. W.; Low, A. C. L.; Li, Y. F. Tetrahedron Lett. 2007, 48, 647-650.
50. (b) Yue, D.; Yao, T.; Larock, R. C. J. Org. Chem. 2005, 70, 10292-10296. Early work:
51. (c) Bew, S. P.; Knight, D. W. Chem. Commun. 1996, 1007-1008.
52. Related metal-catalyzed 5-endo-dig alkyne carbocyclization by reaction with the CH bond: (a) Ajamian, A.; Gleason, J. L. Org. Lett. 2003, 5, 2409-2411.
53. (b) Tanaka, K.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 11492-11493. Ketones:
54. (c) Kel'in, A. V.; Gevorgyan, V. J. Org. Chem. 2002, 67, 95-98. With imines:
55. (d) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075. See also:
56. (e) Smith, C. R.; Bunnelle, E. M.; Rhodes, A. J.; Sarpong, R- Org. Lett. 2007, 9, 1169-1171.
57. 2 to alkynes: (a) Larson, S.; Luidhardt, T.; Kabalka, G. W.; Pagni, R. M. Tetrahedron Lett. 1988, 29, 35-36.
58. (b) Hollins, R. A.; Campos, M. P. A. J. Org. Chem. 1979, 44, 3931-3934. See also:
59. (c) Hénaff, N.; Stewart, S. K.; Whiting, A. Tetrahedron Lett. 1997, 38, 4525-4526.
60. All new compounds gave NMR spectroscopic and analytical or MS data in agreement with their proposed structures. For further details see the Supporting Information.
61. Recent theoretical work on halovinyl and bridged halonium ions: Okazi, T.; Laali, K. K. J. Org. Chem. 2006, 71, 9643-9650.
62. 2, in the presence of the radical inhibitor BHT. The reaction time for the consumption of 1a was the same and 2a was formed in comparable yield. On this basis, we invoke an ionic reaction path.
63. Metal Catalyzed Cross-Coupling Reactions; de Meijere, A., Diederich, F., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
64. 3N at rt, for 1 h.