Synthesis and resolution of benzylisopropylphenylphosphine, a monodentate P-chiral ligand

Tetrahedron Asymmetry

Volumn 11, Issue 16, 2000, Pages 3335-3343

  Albert, Joan ^a   Bosque, Ramón ^a   Cadena, J Magali ^a   Granell, Jaume R ^a   Muller, Guillermo ^a   Ordinas, Juan Ignacio ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOMETALLIC COMPOUND; PHOSPHINE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR OVERHAUSER EFFECT; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; X RAY DIFFRACTION;

EID: 0034714158     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00300-1     Document Type: Article

References (69)

1. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
2. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: Weinheim, 1993.
3. (c) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer Verlag: Berlin, 1999.
4. (a) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375.
5. (b) Kolodiazhni, O. I. Tetrahedron: Asymmetry 1998, 9, 1279.
6. (b) Lagasse, F.; Kagan, H. B. Chem. Pharm. Bull. 2000, 48, 315.
7. (a) Imamoto, T.; Tsuruta, H.; Wada, Y.; Masuda, H.; Yamaguchi, K. Tetrahedron Lett. 1995, 36, 8271.
8. (b) Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
9. (c) Kaloun, E. B.; Merdès, R.; Genêt, J. P.; Uziel, J.; Jugé, S. J. Organomet. Chem. 1997, 529, 455.
10. (d) Jugé, S.; Stephan, M.; Genêt, J. P.; Halut-Desportes, S. J. Chem. Soc., Chem. Commun. 1993. 531.
11. (e) Imamoto, T. Pure Appl. Chem. 1993, 65, 655.
12. (f) Vedrenne, P.; Le Guen, V.; Toupet, L.; Le Gall, T.; Mioskowski, C. J. Am. Chem. Soc. 1999, 121, 1090.
13. (g) Brown, J. M.; Laing, J. C. P. J. Organomet. Chem. 1997, 529, 435.
14. (h) Brunel, J. M.; Faure, B.; Maffei, M. Coord. Chem. Rev. 1998, 665, 178-180.
15. Wolfe B., Livinghouse T. J. Am. Chem. Soc. 120:1998;5116.
16. (a) Leung, P. H.; Liu, A.; Mok, K. F. Tetrahedron: Asymmetry 1999, 10, 1309.
17. (b) Leung, P. H.; Lang, H.; White, A. J. P.; Williams, D. J. Tetrahedron: Asymmetry 1998, 9, 2961.
18. (c) Leung, P. H.; Loh, S. K.; Mok, K. F.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1996, 591.
19. Dunina V.V., Kuz'mina L.G., Rubina M.Y., Grishin Y.K., Veit Y., Kazakova E.I. Tetrahedron: Asymmetry. 10:1999;1483.
20. Albert J., Cadena J.M., Granell J., Muller G., Ordinas J.I., Panyella D., Puerta C., Sañudo C., Valerga P. Organometallics. 18:1999;3511.
21. Moulin, D.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 1999, 10, 4729. Ewalds, R.; Eggeling, E. B.; Hewat, A. C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Chem. Eur. J. 2000, 6, 1496.
22. Moulin, D.; Darcel, C.; Jugé, S. Tetrahedron: Asymmetry 1999, 10, 4729. Ewalds, R.; Eggeling, E. B.; Hewat, A. C.; Kamer, P. C. J.; van Leeuwen, P. W. N. M.; Vogt, D. Chem. Eur. J. 2000, 6, 1496.
23. (a) Albert, J.; Granell, J.; Mínguez, J.; Muller, G.; Sainz, D.; Valerga, P. Organometallics 1997, 16, 3561.
24. (b) Albert, J.; Cadena, J. M.; Granell, J. Tetrahedron: Asymmetry 1997, 8, 991.
25. Chodkiewicz W., Jore D., Wodzki W. Tetrahedron Lett. 12:1979;1069.
26. van Doorn J.A., Meijboom N. Recl. Trav. Chim. Pays-Bas. 111:1992;170.
27. (a) Maitlis, P. M.; Espinet, P.; Russell, M. J. H. In Comprehensive Organometallic Chemistry; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford 1982; Vol. 6, Chapter 38, p 411.
28. (b) Elguero, J.; Fruchier, A.; de la Hoz, A.; Jalón, F.; Manzano, B.; Otero, A.; Gómez de la Torre, F. Chem. Ber. 1996, 129, 384.
29. (c) Crociani, B.; Antonaroli, S.; Paci, M. Organometallics 1997, 16, 384.
30. (a) Wild, S. B. Coord. Chem. Rev. 1997, 166, 291.
31. (b) Robin, F.; Mercier, F.; Ricard, L.; Mathey, F.; Spagnol, M. Chem. Eur. J. 1997, 8, 1365.
32. (c) Dunina, V. V.; Golovan, F. B. Tetrahedron: Asymmetry 1995, 6, 2747.
33. (d) Leung, P.; Quek, G. H.; Lang, H.; Liu, A. M.; Mok, K. F.; White, A. J.; Williams, D. J.; Rees, N.; McFarlane, W. J. Chem. Soc., Dalton Trans. 1998, 1639.
34. (e) Barclay, C. E.; Deeble, G.; Doyle, R. J.; Elix, S. A.; Salem, G.; Jones, T. L.; Wild, S. B.; Willis, A. C. J. Chem. Soc., Dalton Trans. 1995, 57.
35. (f) Pabel, M.; Willis, A. C.; Wild, S. B. Inorg. Chem. 1996, 35, 1244.
36. (g) Chelucci, G.; Cabras, M. A.; Saba, A.; Sechi, A. Tetrahedron: Asymmetry 1996, 7, 1027.
37. (h) Gladiali, S.; Dore, A.; Fabbri, D.; De Lucci, O.; Manassero, M. Tetrahedron: Asymmetry 1994, 5, 511.
38. (i) Chooi, S. Y. M.; Tan, M. K.; Leung, P.; Mok, K. F. Inorg. Chem. 1994, 33, 3096.
39. (j) Pabel, M.; Willis, A. C.; Wild, S. B. Tetrahedron: Asymmetry 1995, 6, 2369.
40. (k) He, G.; Mok, K. F.; Leung, P. H. Organometallics 1999, 18, 4027.
41. (l) Dunina, V. V.; Razmyslova, E. D.; Kuz'mina, L. G.; Churakov, A. V.; Rubina, M. Y.; Grishin, Y. K. Tetrahedron: Asymmetry 1999, 10, 3147.
42. (m) López, C.; Bosque, R.; Sainz, D.; Solans, X.; Font-Bardia, M. Organometallics 1997, 16, 3261.
43. (a) Vila, J. M.; Pereira, M. T.; Ortigueira, J. M.; Graña, M.; Lata, D.; Suárez, A.; Fernández, J. J.; Fernández, A.; López Torres, M.; Adams, H. J. Chem. Soc., Dalton Trans. 1999, 4193.
44. (b) Albert, J.; Granell, J.; Sales, J.; Font-Bardia, M.; Solans, X. Organometallics 1995, 14, 1393.
45. (a) Davies, J. A.; Hartley, F. R. Chem. Rev. 1981, 81, 79.
46. (b) Pearson, R. G. Inorg. Chem. 1973, 12, 712.
47. (c) Navarro, R.; Urriolabeitia, E. P. J. Chem. Soc., Dalton Trans. 1999, 4111. Recently the term transphobia has been proposed to describe the difficulty of coordinating mutually trans phosphine and aryl ligands in palladium complexes
48. (d) Vicente, J.; Abad, J. A.; Frankland, A. D.; Ramírez de Arellano, M. C. Chem. Eur. J. 1999, 5, 3066.
49. (e) Vicente, J.; Arcas, A.; Bautista, D.; Jones, P. G. Organometallics 1997, 16, 2127.
50. (a) Alcock, N. W.; Humes, D. I.; Brown, J. M. J. Chem. Soc., Chem. Commun. 1995, 395.
51. (b) McFarlane, W.; Swarbrick, J. D.; Bookham, J. I. J. Chem. Soc., Dalton Trans. 1998, 3233.
52. (c) Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Tetrahedron: Asymmetry 1993, 4, 743.
53. (d) Berens, U.; Brown, J. M.; Long, J.; Selke, R. Tetrahedron: Asymmetry 1996, 7, 285.
54. (e) Chooi, S. Y. M.; Tan, M. K.; Leung, P. H.; Mok, K. F. Inorg. Chem. 1994, 33, 3096.
55. Aw B.H., Selvaratnam S., Leung P.H., Rees N.H., McFarlane W. Tetrahedron: Asymmetry. 7:1996;1753.
56. (a) Pregosin, P. S.; Rügger, H.; Salzman, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83.
57. (b) Jiang, Q.; Rüegger, H.; Venanzi, L. J. Organomet. Chem. 1995, 488, 233.
58. (c) Giovanett, J. S.; Kelly, C. M.; Landis, C. R. J. Am. Chem. Soc. 1993, 115, 4040.
59. (d) Bookham, J. L.; McFarlane, W. J. J. Chem. Soc., Chem. Commun. 1993, 1352.
60. (e) Blummer, R. E.; Lianza, F.; Pregosin, P. S.; Rügger, H.; Togni, A. Inorg. Chem. 1993, 32, 2663.
61. (f) Aw, B.; Hor, T. S.; Selvaratnam, S.; Mok, K. F., White, A. J. P.; Williams, D. J.; Rees, N. H.; McFarlane, W.; Leung, P. H. Inorg. Chem. 1997, 37, 2138.
62. (g) Leung, P. H.; Quek, G. H.; Lang, H.; 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.
63. (a) Schimdt, R.; Foricher, J.; Cereghetti, M.; Schonholzer, P. Helv. Chim. Acta 1991, 75, 370.
64. (b) Schimdt, R.; Cereghetti, M.; Heiser, B.; Schonholzer, P.; Hausen, H. J. Helv. Chim. Acta 1988, 71, 897.
65. Bosque R., Maseras F. J. Comput. Chem. 21:2000;562.
66. Browning, M. C.; Mellor, J. R.; Morgan, D. J.; Pratt, S. A. J.; Sutton, L. E.; Venanzi, L. J. Chem. Soc. 1962, 693.
67. SPARTAN version 5.0. Wavefunction, Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, U.S.A.
68. Hehre, W. J.; Yu, J.; Adei, E. Abstracts of papers of the ACS 1996, 212, COMP 092.
69. Hehre, W. J.; Yu, J.; Klunziguer, P. E. A Guide to Molecular Mechanics and Molecular Orbital Calculations in Spartan; Wavefunction, Inc., Irvine, 1997.