Asymmetric Pauson-Khand-type reaction mediated by Rh(I) catalyst at ambient temperature

Journal of Organic Chemistry

Volumn 73, Issue 20, 2008, Pages 7985-7989

  Dong, Eun Kim ^a   In, Su Kim ^a   Ratovelomanana Vidal, Virginie ^b   Genêt, Jean Pierre ^b   Jeong, Nakcheol ^a  

^a Korea University   (South Korea)

^b PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL REACTIONS; TEMPERATURE;

AMBIENT TEMPERATURES; CHEMICAL EQUATIONS; PAUSON-KHAND-TYPE REACTION;

RHODIUM;

RHODIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; PAUSON KHAND REACTION; REACTION ANALYSIS;

EID: 53849124716     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801236c     Document Type: Article

References (45)

1. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. Chem. Commun. 1971, 36.
2. (b) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
3. (a) Jeong, N. In Comprehensive Organometallic Chemistry III; Crabtree, R. H., Mingos, M. P., Eds. Elsevier: Oxford, 2006; Vol. 11, pp 335-366.
4. (b) Gibson, S. E.; Mainolfi, N. Angew. Chem., Int. Ed. 2005, 44, 3022.
5. (c) Park, K. H.; Chung, Y. K. Synlett 2005, 545.
6. (d) Boñaga, L. V. R.; Krafft, M. E. Tetrahedron 2004, 60, 9795.
7. (e) Blanco-Urgoiti, J.; Anõrbe, L.; Pérez-Serrano, L.; Domínguez, G.; Pérez-Castells, J. Chem. Soc. Rev. 2004, 33, 32.
8. (f) Gibson, S. E.; Stevenazzi, A. Angew. Chem., Int. Ed. 2003, 42, 1800.
9. (g) Rivero, M. R.; Adrio, J.; Carretero, J. C. Eur. J. Org. Chem. 2002, 2881.
10. (h) Fletcher, A. J.; Christie, S. D. R. J. Chem. Soc., Perkin Trans. 1 2000, 1657.
11. (i) Brummond, K. M.; Kent, J. L. Tetrahedron 2000, 56, 3263.
12. (j) Buchwald, S. L.; Hicks, F. A. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, Heidelberg, 1999; Vol. II, pp 491-510.
13. (k) Ingate, S. T.; Marco-Contelle, J. Org. Prep. Proced. Int. 1998, 30, 121.
14. (l) Chung, Y. K. Coord. Chem. Rev. 1999, 188, 297.
15. (m) Jeong, N. In Transition Metals in Organic Synthesis: Building Blocks and Fine Chemicals; Beller, M., Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, pp 560-577.
16. (a) Gibson, S. E.; Kaufmann, K. A. C.; Loch, J. A.; Steed, J. W.; White, A. J. P. Chem. Eur. J. 2005, 11, 2566.
17. (b) Verdaguer, X.; Lledó, A.; López-Mosquera, C.; Maestro, M. A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 2004, 69, 8053.
18. (c) Konya, D.; Robert, F.; Gimbert, Y.; Greene, A. E. Tetrahedron Lett. 2004, 45, 6975.
19. (d) Gibson, S. E.; Lewis, S. E.; Loch, J. A.; Steed, J. W.; Tozer, M. J. Organometallics 2003, 22, 5382.
20. (e) Verdaguer, X.; Pericàs, M. A.; Riera, A.; Maestro, M. A.; Mahía, J. Organometallics 2003, 22, 1868.
21. (f) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 2002, 67, 3398.
22. (g) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron Lett. 2000, 41, 891.
23. (h) Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron: Asymmetry 2000, 11, 797.
24. (i) Sturla, S. J.; Buchwald, S. L. J. Org. Chem. 1999, 64, 5547.
25. (a) Mandal, S. K.; Amin, S. R.; Crowe, W. E. J. Am. Chem. Soc. 2001, 123, 6457.
26. (b) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026.
27. (c) Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
28. (a) Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771.
29. (b) Jeong, N.; Sung, B. K.; Kim, J. S.; Park, S. B.; Seo, S. D.; Shin, J. Y.; In, K. Y.; Choi, Y. K. Pure Appl. Chem. 2002, 74, 85.
30. (c) Jeong, N.; Kim, D. H.; Choi, J. H. Chem. Commun. 2004, 1134.
31. (d) Jeong, N. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, 2005; Chapter 11, pp 215-240.
32. (a) Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852.
33. (b) Kwong, F. Y.; Lee, H. W.; Lam, W. H.; Qiu, L.; Chan, A. S. C. Tetrahedron: Asymmetry 2006, 17, 1238.
34. (a) Kim, D. E.; Choi, C.; Kim, I. S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Jeong, N. Synthesis 2006, 23, 4053.
35. (b) Kim, D. E.; Choi, C.; Kim, I. S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Jeong, N. Adv. Synth. Catal. 2007, 349, 1999.
36. (a) Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 62, 73.
37. (b) Schmid, T. M.; Consiglio, G. Chem. Commun. 2004, 2318.
38. All molecular geometries incorporating diphosphine ligands in Rh(CO)-Cl(L*) complexes were optimized with the same molecular mechanics program (CAChe Worksystem Pro 5.0). See ref 7b.
39. Andersen, N. G.; Parvez, M.; Keay, B. A. Org. Lett. 2000, 2, 2817.
40. (a) Kwong, F. Y.; Lee, H. W.; Qiu, L.; Lam, W. H.; Li, Y. M.; Kwong, H. L.; Chan, A. S. C. Adv. Synth. Catal. 2005, 347, 1750.
41. (b) Kwong, F. Y.; Li, Y. M.; Lam, W. H.; Qiu, L.; Yeung, C. H.; Chan, K. S.; Chan. A. S. C., Chem. Eur. J. 2005, 11, 3872.
42. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Tetrahedron Lett. 2004, 45, 9163.
43. Shibata, T.; Toshida, N.; Takagi, K. J. Org. Chem. 2002, 67, 7446.
44. Fan, B. M.; Li, S.; Xie, J.; Wang, L.; Tu, Y.; Zhou, Q. L. Science in China, Ser. B: Chem. 2006, 49, 81.
45. Please refer to Supporting Information.