Rhodium-catalyzed chemo-, regio-, and enantioselective [2 + 2 + 2] cycloaddition of alkynes with isocyanates

Organic Letters

Volumn 7, Issue 21, 2005, Pages 4737-4739

  Tanaka, Ken ^a   Wada, Azusa ^a   Noguchi, Keiichi ^a  

^a TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 27144521700     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol052041b     Document Type: Article

References (42)

1. For a review, see: Varela, J. A.; Saà, C. Chem. Rev. 2003, 103, 3787-3801.
2. (a) Hong, P.; Yamazaki, H. Synthesis 1977, 50-52.
3. (b) Hong, P.; Yamazaki, H. Tetrahedron Lett. 1977, 1333-1336.
4. (c) Earl, R. A.; Vollhardt, K. P. C. J. Org. Chem. 1984, 49, 4786-4800.
5. (d) Diversi, P.; Ingrosso, G.; Lucherini, A.; Malquori, S. J. Mol. Catal. 1987, 40, 267-280.
6. (e) Bonaga, L. V. R.; Zhang, H.-C.; Gauthier, D. A.; Reddy, I.; Maryanoff, B. E. Org. Lett. 2003, 5, 4537-4540.
7. (f) Bonaga, L. V. R.; Zhang, H.-C.; Moretto, A. F.; Ye, H.; Gauthier, D. A.; Li, J.; Leo, G. C.; Maryanoff, B. E. J. Am. Chem. Soc. 2005, 127, 3473-3485.
8. (a) Hoberg, H.; Oster, B. W. Synthesis 1982, 324-325.
9. (b) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1982, 234, C35-C38.
10. (c) Hoberg, H.; Oster, B. W. J. Organomet. Chem. 1983, 252, 359-364.
11. (d) Duong, H. A.; Cross, M. J.; Louie, J. J. Am. Chem. Soc. 2004, 126, 11438-11439.
12. (a) Takahashi, T.; Tsai, F.-Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 2002, 124, 5059-5067.
13. (b) Li, Y.; Matsumura, H.; Yamanaka, M.; Takahashi, T. Tetrahedron 2004, 60, 1393-1400.
14. (a) Yamamoto, Y.; Takagishi, H.; Itoh, K. Org. Lett. 2001, 3, 2117-2119.
15. (b) Yamamoto, Y.; Kinpara, K.; Saigoku, T.; Takagishi, H.; Okuda, S.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2005, 127, 605-613.
16. For rhodium-catalyzed cyclotrimerization of alkynes, see: (a) Müller, E. Synthesis 1974, 761-774.
17. (b) Grigg, R.; Scott, R.; Stevenson, P. Tetrahedron Lett. 1982, 23, 2691-2692.
18. (c) Grigg, R.; Scott, R.; Stevenson, P. J. Chem. Soc., Perkin Trans. 1 1988, 1357-1364.
19. (d) Magnus, P.; Witty, D.; Stamford, A. Tetrahedron Lett. 1993, 34, 23-26.
20. (e) Baidossi, W.; Goren, N.; Blum, J. J. Mol. Catal. 1993, 85, 153-162.
21. (f) Doyle, M. P.; Shanklin, M. S. Organometallics 1994, 13, 1081-1088.
22. (g) McDonald, F. E.; Zhu, H. Y. H.; Holmquist, C. R. J. Am. Chem. Soc. 1995, 117, 6605-6606.
23. (h) Kotha, S.; Brahmachary, E. Tetrahedron Lett. 1997, 38, 3561-3564.
24. (i) Witulski, B.; Stengel, T. Angew. Chem., Int. Ed. 1999, 38, 2426-2430.
25. (j) Grigg, R.; Sridharan, V.; Wang, J.; Xu, J. Tetrahedron 2000, 56, 8967-8976.
26. (k) Witulski, B.; Stengel, T.; Fernandez-Hernandez, J. M. Chem. Commun. 2000, 1965-1966.
27. (l) McDonald, F. E.; Smolentsev, V. Org. Lett. 2002, 4, 745-748.
28. (m) Witulski, B.; Zimmermann, A. Synlett 2002, 1855-1859.
29. (n) Witulski, B.; Alayrac, C. Angew. Chem., Int. Ed. 2002, 41, 3281-3284.
30. (o) Nishiyama, H.; Niwa, E.; Inoue, T.; Ishima, Y.; Aoki, K. Organometallics 2002, 21, 2572-2574.
31. (p) Yan, H.; Beatty, A. M.; Fehlner, T. P. Organometallics 2002, 21, 5029-5037.
32. (q) Kinoshita, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2003, 125, 7784-7785.
33. Flynn, S. T.; Hasso-Henderson, S. E.; Parkins, A. W. J. Mol. Catal. 1985, 32, 101-105.
34. Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron. Lett. 1991, 32, 7283-7286.
35. (a) Tanaka, K.; Shirasaka, K. Org. Lett. 2003, 5, 4697-4699.
36. (b) Tanaka, K.; Toyoda, K.; Wada, A.; Shirasaka, K.; Hirano, M. Chem. Eur. J. 2005, 11, 1145-1156.
37. For enantioselective synthesis of axially chiral compounds through [2 + 2 + 2] cycloaddition, see: (a) Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundermann, C. Angew. Chem., Int. Ed. 2004, 43, 3795-3797.
38. (b) Shibata, T.; Fujimoto, T.; Yokota, K.; Takagi, K. J. Am. Chem. Soc. 2004, 126, 8382-8383.
39. (c) Tanaka, K.; Nishida. G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510-6512.
40. (d) Tanaka, K.; Nishida, G.; Ogino, M.; Hirano, M.; Noguchi, K. Org. Lett. 2005, 7, 3119-3121.
41. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264-267.
42. The use of α,ω-diynes, bearing an ortho-halogenated phenyl at the terminal position, is important. The reaction of an o-methyl- or trifluoromethylphenyl-substituted α,ω-diyne furnished a mixture of regioisomers, and an axially chiral regioisomer 10 was a minor product.