Asymmetric synergy between chiral dienes and diphosphines in cationic Rh(I)-catalyzed intramolecular [4 + 2] cycloaddition

Journal of the American Chemical Society

Volumn 128, Issue 39, 2006, Pages 12648-12649

  Aikawa, Kohsuke ^a   Akutagawa, Susumu ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CATION; COORDINATION COMPOUND; DIPHOSPHINE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM; RHODIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; CYCLOADDITION; ELIMINATION REACTION; ENANTIOSELECTIVITY; OXIDATION; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 33749565257     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0650100     Document Type: Article

References (44)

1. (a) Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vols. 1-3.
2. (b) Yamamoto, H. Lewis Acids in Organic Synthesis; Wiley-VCH: New York, 2000; Vols. 1-2.
3. (c) Kobayashi, S.; Jørgensen, K. A. Cycloaddition Reaction in Organic Synthesis; Wiley-VCH: New York, 2002.
4. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
5. Evans, P. A. Modern Rhodium-Catalyzed Organic Reactions; Wiley-VCH: New York, 2005.
6. Intramolecular [4 + 2] cycloaddition: (a) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6432-6434.
7. (b) Jolly, R. S.; Luedtke, G.; Sheehan, D.; Livinghouse, T. J. Am. Chem. Soc. 1990, 112, 4965-4966.
8. (c) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844.
9. (d) Wender, P. A.; Smith, T. E. J. Org. Chem. 1996, 61, 824-825.
10. (e) Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078.
11. (f) Kumar, K.; Jolly, R. S. Tetrahedron Lett. 1998, 39, 3047-3048.
12. (g) Paik, S. J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045-2047.
13. (h) Wang, B.; Cao, P.; Zhang, X. Tetrahedron Lett. 2000, 41, 8041-8044.
14. (i) Motoda, D.; Kinoshita, H.; Shinokubo, H.; Oshima, K. Angew. Chem., Int. Ed. 2004, 43, 1860-1862.
15. (j) Yoo, W. J.; Allen, A.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 5853-5856.
16. (k) Lee, S. I.; Park, S. Y.; Park, J. H.; Jung, I. G.; Choi, S. Y.; Chung, Y. K. J. Org. Chem. 2006, 71, 91-96.
17. (l) Saito, A.; Ono, T.; Takahashi, A.; Taguchi, T.; Hanzawa, Y. Tetrahedron Lett. 2006, 47, 891-895.
18. Intermolecular [4 + 2] cycloaddition: (a) Matsuda, I.; Shibata, M.; Sato, S.; Izumi, Y. Tetrahedron Lett. 1987, 28, 3361-3362.
19. (b) Murakami, M.; Ubukata, M.; Itami, K.; Ito, Y. Angew. Chem., Int. Ed. 1998, 37, 2248-2250.
20. (c) Paik, S. J.; Son, S. U.; Chung, Y. K. Org. Lett. 1999, 1, 2045-2047.
21. For the Rh(I) catalysts, see: (a) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145-6154.
22. (b) O'Mahony, D. J. R.; Belanger, D. B.; Livinghouse, T. Synlett 1998, 443-445.
23. (c) Gilbertson, S. T.; Hoge, G. S.; Genov, D. G. J. Org. Chem. 1998, 63, 10077-10080.
24. (d) Heath, H.; Wolfe, B.; Livinghouse, T.; Bae, S. K. Synthesis 2001, 2341-2347.
25. For the Ir(I) catalysts, see: (e) Shibata, T.; Takasaku, K.; Takesue, Y.; Hirata, N.; Takagi, K. Synlett 2002, 1681-1682.
26. Bakos, J.; Tóth, T.; Heil, B.; Markó, L. J. Organomet. Chem. 1985, 279, 23-29.
27. Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayashi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
28. (a) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460.
29. (b) Lei. A.; He, M.; Zhann, X. J. Am. Chem. Soc. 2002, 124, 8198-8199.
30. (c) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529.
31. Dang, T. P.; Kagan, H. B. J. Chem. Soc., Chem. Commun. 1971, 481-482.
32. Burk, M. J. J. Am. Chem. Soc. 1991, 113, 8518-8519.
33. 1 symmetrical chiral dienes, which were reported by Carreira et al., were selected due to easy preparation from a commercially available carvone: (a) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508-11509.
34. (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc. 2004, 126, 1628-1629.
35. (c) Läng, F.; Breher, F.; Stein, D.; Grützmacher, H. Organometallics 2005, 24, 5148-5158.
36. Fryzuk, M. D.; Bosnich, B. J. Am. Chem. Soc. 1977, 99, 6262-6267.
37. Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, T.; Ito, K.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932-7934.
38. (a) Ohkuma, T.; Ooka, H.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 2675-2676.
39. (b) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40-73.
40. (c) Matsukawa, S.; Mikami, K. Tetrahedron: Asymmetry 1995, 6, 2571-2574.
41. (d) Matsukawa, S.; Mikami, K. Enantiomer 1996, 1, 69-73.
42. (e) Mikami, K.; Matsukawa, S. Nature 1997, 385, 613-615.
43. (f) Mikami, K.; Terada, M.; Korenaga, T.; Matsumoto, Y.; Ueki, M.; Angelaud, R. Angew. Chem., Int. Ed. 2000, 39, 3532-3556.
44. (g) Mikami, K.; Aikawa, K.; Yusa, Y.; Jodry, J. J.; Yamanaka, M. Synlett 2002, 10, 1561-1578.