Organoplatinum complex promoted the asymmetric endo stereochemically controlled Diels-Alder reaction between 3-diphenylphosphinofuran and diphenylvinylphosphine

Inorganic Chemistry

Volumn 48, Issue 23, 2009, Pages 11394-11398

  Liu, Fengli ^a   Pullarkat, Sumod A ^a   Tan, Kien Wee ^a   Li, Yongxin ^a   Leung, Pak Hing ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

3 DIPHENYLPHOSPHINOFURAN; 3-DIPHENYLPHOSPHINOFURAN; CHELATING AGENT; DIPHENYLVINYLPHOSPHINE; FURAN DERIVATIVE; PHOSPHINE DERIVATIVE; PLATINUM COMPLEX; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CHELATING AGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; FURANS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOPLATINUM COMPOUNDS; PHOSPHINES; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 72949089541     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic9014543     Document Type: Article

References (43)

1. (a) Vogel, P.; Cossy, J.; Plumet, J.; Arjona, O. Tetrahedron 1999, 55, 13521.
2. (b) Vogel, P. Curr. Org. Chem. 2000, 4, 455.
3. (c) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48.
4. (d) Arjona, O.; Plumet, J. Curr. Org. Chem. 2002, 6, 571.
5. (e) Robina, I.; Vogel, P. Synthesis 2005, 675.
6. (f) Arjona, O.; Gómez, A. M.; López, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919.
7. (g) Shoji, M.; Yamagushi, J.; Kakeya, H.; Osada, H.; Hayashi, Y. Angew. Chem., Int. Ed. 2002, 41, 3192.
8. (h) Zhou, H. B.; Comninos, J. S.; Stossi, F.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2005, 48, 7261.
9. (i) Chandler, C. L.; Phillips, A. J. Org. Lett. 2005, 7, 3493.
10. (j) Masesane, I. B.; Steel, P. G. Tetrahedron Lett. 2004, 45, 5007.
11. See, for instance, Alkene Metathesis in Organic Synthesis; Furstner, A., Ed.; Springer: New York, 1998. See, in particular, Chapter 1 (by R.R. Schrock) and Chapter 8 (by L. L. Kiesling and L. E. Strong).
12. (a) Arjona, O.; Csákÿ, A. G.; Plumet, J. Eur. J. Org. Chem. 2003, 611.
13. (b) Arjona, O.; Csákÿ, A. G.; Plumet, J. Synthesis 2000, 857.
14. (c) Connon, S. J.; Blechert, S. Angew. Chem., Int. Ed. 2003, 42, 1900.
15. (d) Aljarilla, A.; Plumet, J. Synthesis 2008, 3516.
16. (e) Namboothiri, I. N. N.; Ganesh, M.; Mobin, S. M.; Cojocaru, M. J. Org. Chem. 2005, 70, 2235.
17. (f) Liu, Z.; Rainier, J. D. Org. Lett. 2006, 8, 459.
18. (g) Aljarilla, A.; Plumet, J. Heterocycles 2009, 77, 1333.
19. (h) Araújo, N.; Cumbrera, F. L.; Gil, M. V.; Ortiz, A. L.; Román, E.; Serrano, J. A. Synlett 2008, 5, 687.
20. (i) Ikoma, M.; Oikawa, M.; Sasaki, M. Tetrahedron 2008, 64, 2740.
21. Hockless, D. C.; Gugger, P. A.; Leung, P. H.; Mayadunne, R. C.; Pabel, M.; Wild, S. B. Tetrahedron 1997, 53,4083, and references therein.
22. Doucet, H.; Brown, J. M. Tetrahedron: Asymmetry 1997, 8, 3775.
23. Albert, J.; Cadena, J. M.; Granell, J.; Muller, G.; Ordinas, J. I.; Panyella, D.; Puerta, C.; Sanudo, C.; Valerga, P. Organometallics 1999, 18, 3623.
24. Bienewald, F.; Ricard, L.; Mercier, F.; Mathey, F. Tetrahedron: Asymmetry 1999, 10, 4701.
25. Connolly, D. J.; Lacey, P. M.; McCarthy, M.; Saunders, C. P.; Carroll, A. M.; Goddard, R.; Guiry, P. J. J. Org. Chem. 2004, 69, 6572.
26. Coote, M. L.; Krenske, E. H.; Porter, A.; Weir, M. L.; Willis, A. C.; Zhou, X.; Wild, S. B. Organometallics 2008, 27, 5099.
27. Chooi, S. Y. M.; Leung, P. H.; Lim, C. C.; Mok, K. F.; Quek, G. H.; Sim, K. Y.; Tan, M. K. Tetrahedron: Asymmetry 1992, 3, 529.
28. Kyba, E. P.; Rines, S. P. J. Org. Chem. 1982, 47, 4800.
29. Bookham, J. L.; McFarlane, W. Chem. Commun. 1993, 1352.
30. Aw, B.-H.; Selvaratnam, S.; Leung, P. H.; Rees, N. H.; McFarlane, W. Tetrahedron: Asymmetry 1996, 7, 1753.
31. Aw, B.-H.; Hor, A. T. S.; Selvaratnam, S.; Mok, K. F.; White, A. J. P.; Williams, D. J.; Rees, N. H.; McFarlare, W.; Leung, P. H. Inorg. Chem. 1997, 36, 2138.
32. Leung, P. H.; Selvaratnam, S.; Cheng, C. R.; Mok, K. F.; Rees, N. H.; McFarlane, W. Chem. Commun. 1997, 751.
33. Leung, P. H.; Quek, G. H.; Lang, H. F.; Liu, A. M.; Mok, K. F.; White, A. J. P.; Williams, D. J.; Rees, N. H.; McFarlane, W. J. Chem. Soc., Dalton Trans. 1998, 1639.
34. Leung, P. H.; Ng, K. H.; Li, Y.; White, A. J. P.; Williams, D. J. Chem. Commun. 1999, 2435.
35. Donde, Y.; Overman, L. E. J. Am. Chem. Soc. 1999, 121, 2933.
36. Hollis, T. K.; Overman, L. E. Tetrahedron. Lett. 1997, 38, 8837.
37. Yeo, W. C.; Vittal, J. J.; White, A. J. P.; Williams, D. J.; Leung, P. H. Organometallics 2001, 20, 2167.
38. Yeo, W. C.; Vittal, J. J.; Koh, L. L.; Tan, G. K.; Leung, P. H. Organometallics 2004, 23, 3474.
39. Ma, M.; Pullarkat, S. A.; Li, Y.; Leung, P. H. Inorg. Chem. 2007, 46, 9488.
40. He, G.; Qin, Y.; Mok, K. F.; Leung, P. H. J. Chem. Soc. Chem. Commun. 2000, 167.
41. Liu, F.; Pullarkat, S. A.; Tan, K. W.; Li, Y.; Leung, P. H. Organometallics, DOI: 10.1021/om900586q. Published Online: October 9, 2009.
42. Chooi, S. Y. M.; Ranford, J. D.; Leung, P. H.; Mok, K. F. Tetrahedron: Asymmetry 1994, 5, 1805.
43. Flack, H. D. Acta Crystallogr., Sect. A 1983, 39, 876.