Highly enantioselective synthesis of pseudo-C2-symmetric axially chiral biaryl diphosphines via rhodium-catalyzed double [2 + 2 + 2] cycloaddition

Organometallics

Volumn 27, Issue 19, 2008, Pages 4837-4840

  Doherty, Simon ^a   Smyth, Catherine H ^a   Harrington, Ross W ^a   Clegg, William ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DYES; ENANTIOSELECTIVITY; RHODIUM;

[2+2+2] CYCLOADDITION; DIPHOSPHINES; ENANTIOSELECTIVE SYNTHESES; GOOD YIELDS; HIGH ENANTIOSELECTIVITIES; RHODIUM COMPLEXES;

RHODIUM COMPOUNDS;

EID: 54249097359     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om800755x     Document Type: Article

References (51)

1. (a) Shimizu, H.; Nagasaki, I.; Sayo, N.; Saito, T. In Phosphorus Ligands in Asymmetric Catalysis; Borner, A., Ed.; Wiley-VCH: Weinheim, Germany, 2008; p 207.
2. (b) Li, Y.-M.; Yu, W.-Y.; Chan, A. S. C. Phosphorus Ligands in Asymmetric Catalysis; Borner, A., Ed.; Wiley-VCH: Weinheim, Germany, 2008; p 260.
3. (c) Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Catalysis; Wiley: New York, 1995.
4. (d) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
5. Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
6. (a) Cai, D.; Payack, J. F.; Bender, D. R.; Hughes, D. L.; Verhoeven, T. R.; Reider, P. J. Org. Synth. 1998, 76, 6.
7. (b) Ager, D. J.; East, M. B.; Esienstadt, A.; Laneman, S. A. Chem. Commun. 1997, 2369.
8. (c) Foricher, J.; Heiser, B.; Schmid, R. (Hoffmann-La Roche AG) PCT Int. Appl. WO 9216535, 1992.
9. Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.
10. Kumobayashi, H.; Miura, T.; Sayo, N.; Saito, T.; Zhang, X. Synlett 2001, 1055.
11. For comprehensive and informative reviews see: (a) Tanaka, K. Synlett 2007, 1977.
12. (b) Shibata, T.; Tsuchikama, K. Org. Biomol. Chem. 2008, 6, 1317.
13. For other reviews on transition-metal-catalyzed [2 + 2 + 2] cycloadditions see: (c) Chopade, P. R.; Louie, J. Adv. Synth. Catal. 2006, 348, 2307.
14. (d) Gandon, V.; Aubert, C.; Malacria, M. Chem. Commun. 2006, 2209.
15. (e) Robinson, J. E. In Modern Rhodium-Catalyzed Organic Reactions; Evans, P. A., Ed.; Wiley-VCH: Weinheim, Germany, 2005; p 129.
16. (a) Tanaka, K.; Nishida, G.; Wada, A.; Noguchi, K. Angew. Chem., Int. Ed. 2004, 43, 6510.
17. (b) Tanaka, K.; Nishida, G.; Ogino, M.; Hirano, M.; Noguchi, K. Org. Lett. 2005, 7, 3119.
18. (c) Tanaka, K.; Kamisawa, A.; Suda, T.; Noguchi, K.; Hirano, M. J. Am. Chem. Soc. 2007, 129, 12078.
19. (d) Tanaka, K.; Suda, T.; Noguchi, K.; Hirano, M. Org. Lett. 2007, 72, 2243.
20. (e) Nishida, G.; Suzuki, N.; Noguchi, K.; Tanaka, K. Org. Lett. 2006, 8, 3489.
21. (f) Wada, A.; Noguchi, K.; Hirano, M.; Tanaka, K. Org. Lett. 2007, 9, 1295.
22. For selected examples see: (a) Tsuchikama, K; Kuwata, Y.; Shibata, T. J. Am. Chem. Soc. 2006, 128, 13686.
23. (b) Shibata, T.; Fujimoto, T.; Yokota, K.; Takagi, K. J. Am. Chem. Soc. 2004, 126, 8382.
24. (c) Shibata, T.; Tsuchikama, K.; Otsuka, M. Tetrahedron: Asymmetry 2006, 17, 614.
25. (d) Shibata, T.; Yoshida, S.; Arai, Y.; Otsuka, M.; Endo, K. Tetrahedron 2008, 64, 821.
26. Gutnov, A.; Heller, B.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Sundermann, B.; Sundennann, C. Angew. Chem., Int. Ed. 2004, 43, 3745.
27. (a) Doherty, S.; Knight, J. G.; Robins, E. G.; Scanlan, T. H.; Champkin, P. A.; Clegg, W. J. Am. Chem. Soc. 2001, 123, 5110.
28. (b) Doherty, S.; Robins, E. G.; Nieuwenhuyzen, M.; Knight, J. G.; Champkin, P. A.; Clegg, W. Organometallics 2002, 21, 1383.
29. (c) Doherty, S.; Newman, C. R.; Rath, R. K.; van den Berg, J.-A.; Hardacre, C.; Nieuwenhuyzen, M.; Knight, J. G. Organometallics 2004, 23, 1055.
30. (d) Doherty, S.; Newman, C. R.; Rath, R. K.; Luo, K.-K.; Nieuwenhuyzen, M.; Knight, J. G. Org. Lett. 2003, 5, 3863.
31. (e) Doherty, S.; Goodrich, P.; Hardacre, C.; Luo, H.-K.; Rooney, D. W.; Seddon, K.; Styring, P. Green Chem. 2004, 6, 63.
32. (f) Doherty, S.; Knight, J. G.; Hardacre, C.; Luo, H.-K.; Newman, C. R.; Rath, R. K.; Campbell, S.; Nieuwenhuyzen, M. Organometallics 2004, 23, 6127.
33. (g) Doherty, S.; Goodrich, P.; Hardacre, C.; Luo, H.-K.; Nieuwenhuyzen, M.; Rath, R. K. Organometallics 2005, 24, 5945.
34. (h) Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. J. Org. Chem. 2006, 71, 9751.
35. (i) Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. Organometallics 2007, 26, 6453.
36. (j) Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. Organometallics 2007, 26, 5961.
37. Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. Org. Lett. 2007, 9, 4925.
38. Kondoh, A.; Yorimitsu, H.; Oshima, K. J. Am. Chem. Soc. 2007, 129, 6996.
39. For the synthesis of racemic biaryl monophosphines via Diels-Alder cycloaddition see: (a) Ashburn, B. O.; Carter, R. G. Angew. Chem., Int. Ed. 2006, 45, 6737.
40. (b) Ashburn, B. O.; Carter, R. G. J. Am. Chem. Soc. 2007, 129, 9109.
41. Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2007, 46, 3951.
42. Heller, B.; Gutnov, A.; Fischer, C.; Drexler, H.-J.; Spannenberg, A.; Redkin, D.; Sundermann, C.; Sundermann, B. Chem. Eur. J. 2007, 13, 1117.
43. For the synthesis of axially chiral biaryl monophosphonates via asymmetric Suzuki-Miyaura cross coupling see: Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 12051.
44. Nishida, G.; Noguchi, K.; Hirano, M.; Tanaka, K. Angew. Chem., Int. Ed. 2008, 47, 3410.
45. Huang, Y.-D.; Yu, H.-T.; Meng, J.-B.; Wang, Y.-M. Chin. J. Struct. Chem. 2002, 149, 21.
46. Huang, Y.-D.; Yu, H.-T.; Meng, J.-B.; Metsuura, T.; Wang, Y.-M. J. Mol. Struct. 2002, 610, 247.
47. Nishida, G.; Ogaki, S.; Yusa, Y.; Yokozawa, T.; Noguchi, K.; Tanaka, K. Org. Lett. 2008, 10, 2849.
48. Bringmann, G.; Price Mortimer, A. J.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
49. 11 and related axially chiral biaryl diphosphines:
50. (a) Mikami, K.; Aikawa, K.; Kainuma, S.; Kawakami, Y.; Saito, T;. Sayo, N.; Kumobayashi, H. Tetrahedron: Asymmetry 2004, 15, 3885.
51. (b) Aikawa, K.; Kainuma, S.; Hatano, M.; Mikami, K. Tetrahedron Lett. 2004, 45, 183.