Rhodium-catalyzed intramolecular alkyne-carbodiimide Pauson-Khand-type reaction

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1239-1241

  Saito, Takao ^a   Sugizaki, Katsuya ^a   Otani, Takashi ^a   Suyama, Toshiyuki ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147210204     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol063123i     Document Type: Article

References (61)

1. (a) Saito, T.; Ohkubo, T.; Kuboki, H.; Maeda, M.; Tsuda, K.; Karakasa, T.; Satsumabayashi, S. J. Chem. Soc., Perkin Trans. 1 1998, 3065.
2. (b) Saito, T.; Tsuda, K. Tetrahedron Lett. 1996, 37, 9071.
3. (c) Saito, T.; Tsuda, K.; Saito, Y. Tetrahedron Lett. 1996, 37, 209.
4. (d) Saito, T.; Ohmori, H.; Ohkubo, T.; Motoki, S. Chem. Commun. 1993, 1802.
5. (e) Saito, T.; Ohkubo, T.; Maruyama, K.; Kuboki, H.; Motoki, S. Chem. Lett. 1993, 1127.
6. (f) Saito, T.; Ohmori, H.; Furuno, E.; Motoki, S. Chem. Commun. 1992, 22.
7. (g) Saito, T.; Nakane, M.; Miyazaki, T.; Motoki, S. J. Chem. Soc., Perkin Trans. 1 1989, 2140.
8. (h) Saito, T.; Nakane, M.; Endo, M.; Yamashita, H.; Oyamada, Y.; Motoki, S. Chem. Lett. 1986, 135.
9. For reviews on the Pauson-Khand reaction: (a) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800. (catalytic)
10. (b) Blanco-Urgoiti, J.; Anorbe, L.; Perez-Serrano, L.; Dominguez, G.; Perez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
11. (c) Rivero, M. R.; Adrio, J.; Carretero, J. C. Eur. J. Chem. 2002, 2881.
12. (d) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Chem.-Eur. J. 2001, 7, 1589.
13. (e) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
14. (f) Jeong, N. In Transition Metals in Organic Synthesis; Beller, M., Bolm, C., Eds; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 560-577.
15. (g) Schore, N. E. Org. React. 1991, 40, 1.
16. (h) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. 1998, 37, 911.
17. (i) Frühauf, H.-W. Chem. Rev. 1997, 97, 523.
18. (j) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans, 1 2000, 1657.
19. (k) Hanson, B. E. Comments Inorg. Chem. 2002, 23, 289.
20. For carbonyl Pauson-Khand, see: (a) Kablaouli, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182.
21. (b) Kablaouli, N. M.; Hick, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818.
22. (c) Cowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557.
23. (d) MandalK, S. K.; Amin, S. R.; Crowe, W. E. J. Am. Chem. Soc. 2001, 123, 6457.
24. (e) Yu, C.-M.; Hong, Y.-T.; Lee, J.-H. J. Org. Chem. 2004, 69, 8506.
25. (f) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
26. (g) Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Chem. Commun. 2005, 3295.
27. (h) Kang, S.-K.; Kim, K.-J.; Hong, Y.-T. Angew. Chem. 2002, 114, 1654.
28. For imine Pauson-Khand, see: (i) Imhof, W.; Anders, E.; Göbel, A.; Görls, H. Chem.-Eur. J. 2003, 9, 1166.
29. (j) Göbel, A.; Imhof, W. Chem. Commun. 2001, 593.
30. (a) Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev. 2000, 100, 3067.
31. (b) The Chemistry of Ketenes, Allenes, and Related Compounds; Patai, S., Ed.; John Wiley & Sons: New York, 1980; Part 1 & 2.
32. (c) Modern Allene Chemistry; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, 2004.
33. (d) Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
34. For a review on allenic Pauson-Khand reactions, see: Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2004, 3377.
35. For selected recent reports on allenic Pauson-Khand reactions, see (allene-ene): (a) Wender, P. A.; Croatt, M. P.; Deschamps, N. M. Angew. Chem., Int. Ed. 2006, 45, 2459. (allene-yne):
36. (b) Mukai, C.; Hirose, T.; Teramoto, S.; Kitagaki, S. Tetrahedron 2005, 61, 10983.
37. (c) Mukai, C.; Inagaki, F.; Yoshida, T.; Yoshitani, K.; Hara, Y.; Kitagaki, S. J. Org. Chem. 2005, 70, 7159.
38. (d) Mukai, C.; Inagaki, F.; Yoshida, T.; Kitagaki, S. Tetrahedron Lett. 2004, 45, 4117.
39. (e) Shibata, T.; Kadowaki, S.; Hirase M.; Takagi, K. Synlett 2003, 573.
40. (f) Narasaka, K.; Shibata, T. Chem. Lett. 1994, 315. (allenic, first report):
41. (g) Shibata, T.; Koga, Y.; Narasaka, K. Bull. Chem. Soc. Jpn. 1994, 68, 911.
42. (h) Brummond, K. M.; Chen, H.; Fisher, K. D.; Kerekes, A. D.; Rickards, B.; Still, P. C.; Geib, S. J. Org. Lett. 2002, 4, 1931.
43. (i) Brummond, K. M.; Kerekes, A. D.; Wan, H. J. Org. Chem. 2002, 67, 5156.
44. (j) Anorbe, L.; Poblador, A.; Dominguez, G.; Perez-Castells, J. Tetrahedron Lett. 2004, 45, 4441.
45. (k) Alcaide, B.; Almendros, P.; Allagoncillo, C. Chem.-Eur. J. 2002, 8, 1719.
46. (l) Cao, H.; Flippen-Anderson, J.; Cook, J. M. J. Am. Chem. Soc. 2003, 125, 3230.
47. (m) Pagenkopf, B. L.; Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Synthesis 2000, 1009. (inter allene-yne):
48. (n) Antras, F.; Ahmar, M.; Cazes, B. Tetrahedron Lett. 2001, 42, 8153.
49. (o) Antras, F.; Ahmar, M.; Cazes, B. Tetrahedron Lett. 2001, 42, 8157. (allenecarbonyl):
50. 3e
51. 3h
52. 5, which afforded indeed a Pauson-Khand-type product in a reasonable yield: Ohshiro, Y.; Kinugasa, K.; Minami, T.; Agawa, T. J. Org. Chem. 1970, 35, 2136.
53. (b) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35.
54. (c) Very recently, Rucatalyzed intermolecular Pauson-Khand-type cocyclization of isocyanates has been reported. Kondo, T.; Nomura, M.; Ura, Y.; Wada, K.; Mitsudo, T. J. Am. Chem. Soc. 2006, 128, 14816.
55. Saito, T.; Shiotani, M.; Otani, T.; Hasaba, S. Heterocycles 2003, 60, 1045. The catalytic version of this research was presented at: 85th Annual Meeting of the Chemical Society of Japan, Yokohama, March, 2005; Abstract 1B2-25. 35th Congress of Heterocyclic Chemistry, Osaka, October, 2005; Abstract 2C-08. The International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, December, 2005; Abstract ORGN 1696.
56. 8 and a tetramethylthiourea promoter (60-120 mol %) were successfully applied. Mukai, C.; Yoshida, T.; Sorimachi, M.; Odani, A. Org. Lett. 2006, 8, 83.
57. (a) Jeong, N.; Lee, S.; Sung, B.-K. Organometallics 1998, 17, 3642.
58. (b) Jeong, N.; Seo, S. D.; Shin, J. Y. J. Am. Chem. Soc. 2000, 122, 10220.
59. For a Pauson-Khand reaction using a Rh(I) complex catalyst, see: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
60. Mukai, C.; Nomura, I.; Yamanishi, K.; Hanaoka, M. Org. Lett. 2002, 4, 1755. Refs 5b-d.
61. Kurzer, F.; Douraghi-Zadeh, K. Chem. Rev. 1967, 67, 107.