Cycloisomerization of enynes via rhodium vinylidene-mediated catalysis

Journal of the American Chemical Society

Volumn 127, Issue 29, 2005, Pages 10180-10181

  Kim, Hahn ^a   Lee, Chulbom ^a  

^a PRINCETON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ENYNE DERIVATIVE; RHODIUM DERIVATIVE; RHODIUM VINYLIDENE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CYCLIZATION; ISOMERIZATION; REACTION ANALYSIS; SCREENING; TEMPERATURE DEPENDENCE;

EID: 22944488016     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052775j     Document Type: Article

References (47)

1. For recent reviews, see: (a) Lloyd-Jones, G. C. Org. Biomol. Chem. 2003, 1, 215.
2. (b) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813.
3. Trost, B. M.; Krische, M. J. Synlett 1998, 1.
4. Pd: (a) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781.
5. (b) Trost, B. M.; Tanoury, G. J.; Lautens, M.; Chan, C.; MacPherson, D. T. J. Am. Chem. Soc. 1994, 116, 4255.
6. Co: (c) Llerena, D.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1996, 37, 7027.
7. (d) Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Bonaga, L. V. R.; Cheung, Y. Y.; Fu, Z.; Shao, B.; Scott, I. L. Tetrahedron Lett. 1998, 39, 5911.
8. Ni-Cr: (e) Trost, B. M.; Tour, J. M. J. Am. Chem. Soc. 1987, 109, 5268.
9. Ru: (f) Kinoshita, A.; Mori, M. Synlett 1994, 1020.
10. (g) Chatani, N.; Morimoto, T.; Muto, T.; Murai, S. J. Am. Chem. Soc: 1994, 116, 6049.
11. (h) Trost, B. M.; Toste, F. D. J. Am. Chem. Soc. 2000, 122, 714.
12. Ir: (i) Chatani, N.; Inoue, H.; Morimoto, T.; Muto, T.; Murai, S. J. Org. Chem. 2001, 66, 4433.
13. Ti: (j) Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
14. Rh: (k) Cao, P.; Wang, B.; Zhang, X. J. Am. Chem. Soc. 2000, 122, 6490.
15. (a) Echavarren, A. M.; Nevado, C. Chem. Soc. Rev. 2004, 33, 431.
16. (b) Nieto-Oberhuber, C.; Muñoz, M. P.; Buñuel, E.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. Angew. Chem., Int. Ed. 2004, 43, 2402.
17. (c) Méndez, M.; Mamane, V.; Fürstner, A. Chemtracts 2003, 16, 397.
18. (d) Oi, S.; Tsukamoto, I.; Miyano, S.; Inoue, Y. Organometallics 2001, 20, 3704.
19. (e) Fürstner, A.; Stelzer, F.; Szillat, H. J. Am. Chem. Soc. 2001, 123, 11863.
20. (f) Fürstner, A.; Szillat, H.; Gabor, B.; Mynott, R. J. Am. Chem. Soc. 1998, 120, 8305.
21. (g) Chatani, N.; Furukawa, N.; Sakurai, H.; Murai, S. Organometallics 1996, 15, 901.
22. For reviews, see: (a) Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317.
23. (b) Poulsen, C. S.; Madsen, R. Synthesis 2003, 1.
24. Mori, M. Top. Organomet. Chem. 1998, 1, 133.
25. For reviews on metal vinylidene chemistry, see: (a) Bruce, M. I. Chem. Rev. 1991, 91, 197.
26. (b) Bruce, M. I.; Swincer, A. G. Adv. Organomet. Chem. 1983, 22, 59.
27. For recent reviews on the catalysis of metal vinylidenes, see: (c) Bruneau, C. Top. Organomet. Chem. 2004, 11, 125.
28. Trost, B. M. Acc. Chem. Res. 2002, 35, 695.
29. (e) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
30. (a) Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319.
31. (b) Maeyama, K.; Iwasawa, N. J. Org. Chem. 1999, 64, 1344.
32. Madhushaw, R. J.; Lo, C.-Y.; Hwang, C.-W.; Su, M.-D.; Shen, H.-C.; Pal, S.; Shaikh, I. R.; Liu, R.-S. J. Am. Chem. Soc. 2004, 126, 15560.
33. For the use of this catalyst system to form rhodium vinylidenes, see: (a) Trost, B. M.; Rhee, Y. H. J. Am. Chem. Soc. 2003, 125, 7482.
34. (b) Ohmura, T.; Yamamoto, Y.; Miyaura, N. J. Am. Chem. Soc. 2000, 122, 4990.
35. Grigg, R.; Stevenson, P.; Worakun, T. Tetrahedron 1988, 44, 4967.
36. 7 suggests that the incomplete deuterium incorporation is mainly due to an H/D exchange between the alkyne and adventitious water. See Supporting Information for details. For similar observations, see: (a) Yeh, K.-L.; Liu, B.; Lo, C.-Y.; Liu, R.-S. J. Am. Chem. Soc. 2002, 124, 6510.
37. (b) Odedra, A.; Wu, C.-J.; Pratap, T. B.; Huang, C.-W.; Ran, Y.-F.; Liu, R.-S. J. Am. Chem. Soc. 2005, 127, 3406 and references therein.
38. For examples of intermolecular [2 + 2] cycloaddition of Ru vinylidenes, see: (a) Murakami, M.; Ubukata, M.; Ito, Y. Tetrahedron Lett. 1998, 39, 7361.
39. (b) Murakami, M.; Hori, S. J. Am. Chem. Soc. 2003, 125, 4720.
40. For an intramolecular stoichiometric example using a Ti vinylidene, see: (c) Dennehy, R. D.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1990, 1060.
41. For a mechanistic discussion of this type of β-hydrogen elimination, see: Johnson, T. H.; Cheng, S.-S. J. Am. Chem. Soc. 1979, 101, 5277.
42. For a Ru vinylidene formation via selenyl migration, see: Hill, A. F.; Hulkes, L. G.; White, A. J. P.; Williams, D. J. Organometallics 2000, 19, 370.
43. (a) Miura, T.; Iwasawa, N. J. Am. Chem. Soc. 2002, 124, 518.
44. (b) Dankwardt, J. W. Tetrahedron Lett. 2001, 42, 5809.
45. (c) Katayama, H.; Ozawa, F. Organometallics 1998, 17, 5190.
46. Onitsuka, K.; Katayama, H.; Sonogashira, K.; Ozawa, F. J. Chem. Soc., Chem. Commun. 1995, 2267.
47. (e) Werner, H.; Baum, M.; Schneider, D.; Windmuller, B. Organometallics 1994, 13, 1089.