Synthesis and first application of a new family of monophosphine ferrocene ligands (MOPF)

Chemical Communications

Volumn , Issue 24, 1999, Pages 2517-2518

  Pedersen, Henriette L ^a   Johannsen, Mogens ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033592934     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a908921g     Document Type: Article

References (23)

1. For some examples where monophosphine ligands or ligands with a phosphine and a hemilabile coordinating group are superior to the usual bisphosphines, see e.g.: (a) Asymmetric hydrosilylation: Y. Uozumi and T. Hayashi, J. Am. Chem. Soc., 1991, 113, 9887;
2. (b) Asymmetric hydrovinylation: T. V. RajanBabu, N. Nomura, J. Jin, B. Radetich, H. Park and M. Nandi, Chem. Eur. J., 1999, 5, 1963;
3. (c) Asymmetric Grignard cross-coupling: T. Hayashi, K. Hayashizaki, T. Kiyoi and Y. Ito, J. Am. Chem. Soc., 1988, 110, 8153.
4. For the synthesis and application of MOP and other monophosphine ligands see e.g.: (a) Y. Uozumi, A. Tanahashi, S.-Y. Lee and T. Hayashi, J. Org. Chem., 1993, 58, 1945;
5. (b) K. Kitayama, Y. Uozumi and T. Hayashi, J. Chem. Soc., Chem. Commun., 1995, 1533;
6. (c) H. Tye, D. Smyth, C. Eldred and M. Wills, Chem. Commun., 1997, 1053;
7. (d) C. D. Graf, C. Malan, K. Harms and P. Knochel, J. Org. Chem., 1999, 64, 5581;
8. (e) G. Zhu, Z. Chen, Q. Jiang, D. Xiao, P. Cao and X. Zhang, J. Am. Chem. Soc., 1997, 119, 3836;
9. (f) B. L. Feringa, M. Pineschi, L. A. Arnold, R. Imbos and A. H. M. de Vries, Angew. Chem., Int. Ed. Engl., 1997, 36, 2620;
10. (g) B. Bartels and G. Helmchen, Chem. Commun., 1999, 741.
11. The MOPF ligands are structurally different from known ferrocene monophosphines which have a methylene spacer group next to the phosphine. See e.g. T. Hayashi, in Ferrocenes, ed. A. Togni and T. Hayashi, VCH, Weinheim, 1995, p. 118.
12. (a) O. Riant, G. Argourch, D. Guillaneux, O. Samuel and H. B. Kagan, J. Org. Chem., 1998, 63, 3511;
13. (b) D. H. Hua, N. M. Lagneau, Y. Chen, P. M. Robben, G. Clapham and P. D. Robinson, J. Org. Chem., 1996, 61, 4508;
14. (c) M. Tsukazaki, M. Tinkl, A. Roglans, B. J. Chapell, N. J. Taylor and V. Snieckus, J. Am. Chem. Soc., 1996, 118, 685;
15. (d) For references prior to 1996 see: A. Togni, Angew. Chem., 1996, 108, 1581.
16. D. Price and N. S. Simpkins, Tetrahedron Lett., 1995, 36, 6135.
17. F. Rebière, O. Riant, L. Richard and H. B. Kagan, Angew. Chem., 1993, 105, 644.
18. For other asymmetric hydrosilylation reactions of styrene see e.g.: G. Bringmann, A. Wuzik, M. Breuning, P. Henschel, K. Peters and E.-M. Peters, Tetrahedron: Asymmetry, 1999, 10, 3025; G. Pioda and A. Togni, Tetrahedron: Asymmetry, 1999, 9, 3903; T. Okada, T. Morimoto and K. Achiwa, Chem. Lett., 1990, 999.
19. For other asymmetric hydrosilylation reactions of styrene see e.g.: G. Bringmann, A. Wuzik, M. Breuning, P. Henschel, K. Peters and E.-M. Peters, Tetrahedron: Asymmetry, 1999, 10, 3025; G. Pioda and A. Togni, Tetrahedron: Asymmetry, 1999, 9, 3903; T. Okada, T. Morimoto and K. Achiwa, Chem. Lett., 1990, 999.
20. For other asymmetric hydrosilylation reactions of styrene see e.g.: G. Bringmann, A. Wuzik, M. Breuning, P. Henschel, K. Peters and E.-M. Peters, Tetrahedron: Asymmetry, 1999, 10, 3025; G. Pioda and A. Togni, Tetrahedron: Asymmetry, 1999, 9, 3903; T. Okada, T. Morimoto and K. Achiwa, Chem. Lett., 1990, 999.
21. This selectivity has been shown to be substrate dependent. MeO-MOP generally gave better results than H-MOP using non-styrene-type substrates such as e.g. oct-1-ene (up to 96% ee) [ref. 2(b)]. We are currently investigating the MOPF ligands to see whether they display similar behaviour.
22. 3). Spectroscopic data were in accordance with those from a commercial sample.
23. During the course of our investigation we became aware of a paper from another group synthesising related benzene chromium tricarbonyl complexes. This prompted us to report our findings at this early stage. See: S. C. Nelson and M. A. Hilfiker, Org. Lett., 1999, 1, 1379.