Rhodium-catalyzed functionalization of sterically hindered alkenes

Organic Letters

Volumn 12, Issue 2, 2010, Pages 308-310

  Gendrineau, Thomas ^a   Genet, Jean Pierre ^a   Darses, Sylvain ^a  

^a PSL RESEARCH UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORANE DERIVATIVE; ORGANOMETALLIC COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; BORANES; CATALYSIS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM;

EID: 74949108453     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902646j     Document Type: Article

References (57)

1. Reviews: (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033.
2. (b) Hayashi, T.; Yamasaki, K. Chem. Rev. 2003, 103, 2829.
3. (c) Guo, H.C.; Ma, J.-A. Angew. Chem., Int. Ed. 2006, 45, 354.
4. (d) Miura, T.; Murakami, M. Chem. Commun. 2007, 217.
5. (e) Yamamoto, Y.; Nishikata, T.; Miyaura, N. Pure. Appl. Chem 2008, 80, 807.
6. (f) Alexakis, A.; Bäckvall, J.-.E.; Krause, N.; Pàmies, O.; Diéguez, M. Chem. Rev. 2008, 108, 2796.
7. (g) Harutyunyan, S. R.; den Hartog, T.; Geurts, K.; Minnaard, A. J.; Feringa, B. L. Chem. Rev. 2008, 108, 2824.
8. (h) von Zezschwitz, P. Synthesis 2008, 1809.
9. (i) Gutnov, A. Eur. J. Org. Chem. 2008, 4547.
10. (a) Wu, J.; Mampreian, D. M.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 4584.
11. (b) d'Augustin, M.; Palais, L.; Alexakis, A. Angew. Chem., Int. Ed 2005, 44, 1376.
12. (c) Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 14988.
13. (d) Martin, D.; Kehrli, S.; d'Augustin, M.; Clavier, H.; Mauduit, M.; Alexakis, A. J. Am Chem. Soc. 2006, 128, 8416.
14. (e) Lee, K.-s.; Brown, M. K.; Hird, A. W.; Hoveyda, A. H. J. Am. Chem. Soc. 2006, 128, 7182.
15. (f) Palais, L.; Mikhel, I. S.; Bournaud, C.; Micouin, L.; Falciola, C A.; Vuagnoux-d'Augustin, M.; Rosset, S.; Bernardinelli, G.; Alexakis, A. Angew. Chem., Int. Ed. 2007, 46, 7462.
16. (g) Brown, M. K.; May, T. L.; Baxter, C A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 1097.
17. (h) Hawner, C.; Li, K.; Cirriez, V.; Alexakis, A. Angew. Chem., Int. Ed. 2008, 47, 8211.
18. For some recent examples of stoichiometric addition of organometallics to α/β-unsaturated tri- or tetrasubstituted alkenes, see: (a) Toyooka, N.; Fukutome, A.; Shinoda, H.; Nemoto, H. Tetrahedron 2004, 60, 6197.
19. (b) Becheanu, A.; Baro, A.; Laschat, S.; Frey, W. Eur. J. Org. Chem. 2006, 2215.
20. (c) Oueslati, F.; Perrio, C.; Dupas, G.; Barré, L. Org. Lett. 2007, 9, 153.
21. (d) Zimmerman, H. E.; Suryanarayan, V. Eur. J. Org. Chem. 2007, 4091, and references cited therein.
22. (a) Fillion, E.; Wilsily, A. J. Am. Chem. Soc. 2006, 128, 2774.
23. (b) Wilsily, A.; Fillion, E. Org. Lett. 2008, 10, 2801.
24. Mauleón, P.; Carretero, J. C. Chem. Commun. 2005, 4961.
25. (a) Shintani, R.; Duan, W.-.L.; Hayashi, T. J. Am. Chem. Soc. 2006, /28, 5628.
26. (b) Shintani, R.; Tsutsumi, Y.; Nagaosa, M.; Nishimura, T.; Hayashi, T. J. Am. Chem. Soc. 2009, 131, 13588.
27. Collier, P. N. Tetrahedron Lett. 2009, 50, 3909.
28. Sörgel, S.; Tokunaga, N.; Sasaki, K.; Okamoto, K.; Hayashi, T. Org. Lett. 2008, 10, 589.
29. Fillion, E.; Carret, S.; Mercier, L. G.; Trépanier, V. É. Org. Lett. 2008, 10, 437.
30. de la Herran, G.; Mba, M.; Murcia, M. C.; Plumet, J.; Csaḱy, A. G. Org. Lett. 2005, 7, 1669.
31. Belyk, K. M.; Beguin, C. D.; Palucki, M.; Grinberg, N.; Da Silva, J.; Askin, D.; Yasuda, N. Tetrahedron Lett. 2004, 45, 3265.
32. (a) Pucheault, M.; Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2002, 3552.
33. (b) Navarre, L.; Darses, S.; Genet, J.-P. Angew. Chem., Int. Ed. 2004, 43, 719.
34. (c) Pucheault, M.; Darses, S.; Genet, J.-P. J. Am. Chem. Soc. 2004, 126, 15356.
35. (d) Pucheault, M.; Darses, S.; Genet, J.-P. Chem. Commun. 2005, 4714.
36. (e) Mora, G.; Darses, S.; Genet, J.-P. Adv. Synth. Catal. 2007, 349, 1180.
37. (f) Martinez, R. m.; Voica, F.; Genet, J.-P.; Darses, S. Org. Lett. 2007, 9, 3213.
38. (g) Navarre, L.; Martinez, R. m.; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159.
39. (a) Navarre, L.; Darses, S.; Genet, J.-P. Chem Commun. 2004, 1108.
40. (b) Navarre, L.; Darses, S.; Genet, J.-P. Adv. Synth. Catal., 2006, 348, 317.
41. (c) Gendrineau, T.; Demoulin, N.; Navarre, L.; Genet, J.-P.; Darses, S. Chem.-Eur. J. 2009, 15, 4710.
42. (a) Srikanth, G. S. C.; Castle, S. L. Tetrahedron 2005, 67, 10377.
43. (b) Yamamoto, Y.; Nishikata, T.; Miyaura, N. J. Synth. Org. Chem. Jpn. 2006, 64, 1112.
44. (c) Yamamoto, Y.; Nishikata, T.; Miyaura, N. Pure Appl. Chem. 2008, 80, 807.
45. Reviews: (a) Darses, S.; Genet, J.-P. Eur. J. Org. Chem. 2003, 4313.
46. (b) Molander, G. A.; Figueroa, R. Aldrichim. Acta 2005, 38, 49.
47. (c) Molander, G. A.; Ellis, N. M. Acc. Chem. Res. 2007, 40, 275.
48. (d) Stefani, H. A.; Cella, R.; Vieira, A. S. Tetrahedron 2007, 63, 3623.
49. (e) Darses, S.; Genet, J.-P. Chem. Rev. 2008, 108, 288.
50. 3N, see: (a) Lalic, G.; Corey, E. J. Org. Lett. 2007, 9, 4921.
51. (b) Lalic, G.; Corey, E. J. Tetrahedron Lut. 2008, 49, 4894.
52. (c) Gendrineau, T.; Genet, J.-P.; Darses, S. Org. Lett. 2009, 11, 3486.
53. Gendrineau, T.; Chuzel, O.; Eijsberg, H.; Genet, J.-P.; Darses, S. Angew. Chem., Int. Ed. 2008, 47, 7669, and references cited therein.
54. For the use of chiral dienes in catalysis, see: (a) Hayashi, T.; Ueyama, K.; Tokunaga, N.; Yoshida, K. J. Am. Chem. Soc. 2003, 125, 11508.
55. (b) Fischer, C.; Defieber, C.; Suzuki, T.; Carreira, E. M. J. Am. Chem. Soc 2004, 126, 1628.
56. (c) Review: Defieber, C.; Grützmacher, H.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 4482.
57. Hayashi, T.; Takahashi, M.; Takaya, Y.; Ogasawara, M. J. Am. Chem. Soc. 2002, 124, 5052.