Bipnor: A new, efficient bisphosphine having two chiral, nonracemizable, bridgehead phosphorus centers for use in asymmetric catalysis

Chemistry - A European Journal

Volumn 3, Issue 8, 1997, Pages 1365-1369

  Robin, Frédéric ^a   Mercier, François ^a   Ricard, Louis ^a   Mathey, François ^a   Spagnol, Michel ^b  

^a LABORATOIRE HÉTÉROÉLÉMENTS ET COORDINATION   (France)

^b SANOFI   (France)

Author keywords

Asymmetric catalysis; Hydrogenations; Palladium; Phosphorus ligands; Rhodium

Indexed keywords

EID: 0030799832     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970030824     Document Type: Article

References (28)

1. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori J. Am. Chem. Soc. 1980, 102, 7934; for a review, see: R. Noyori, H. Takaya Acc. Chem. Res. 1990, 23, 345.
2. A. Miyashita, A. Yasuda, H. Takaya, K. Toriumi, T. Ito, T. Souchi, R. Noyori J. Am. Chem. Soc. 1980, 102, 7934; for a review, see: R. Noyori, H. Takaya Acc. Chem. Res. 1990, 23, 345.
3. M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518.
4. For a recent review, see: K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375.
5. W. S. Knowles, Acc. Chem. Res. 1983, 16, 106.
6. F. Mathey, F. Mercier, C. Charrier, J. Fischer, A. Mitschier, J. Am. Chem. Soc. 1981, 103, 4595.
7. F. Laporte, F. Mercier, L. Ricard, F. Mathey, Bull. Soc. Chim. Fr. 1993, 130, 843.
8. F. Mathey, D. Neibecker, A. Brèque (SNPE), Fr. Pat. 2588197, Oct. 3, 1985; Chem. Abstr. 1987, 107, 219468v.
9. D. Neibecker, R. Reau, Angew. Chem. Int. Ed. Engl. 1989, 28, 500.
10. W. A. Herrmann, C. W. Kohlpaintner, R. B. Manatsberger, H. Bahrmann, H. Kottmann J. Mol. Catal. A 1995, 97, 65.
11. S. Lelièvre, F. Mercier, F. Mathey, J. Org. Chem. 1996, 61, 3531.
12. It must be noted here that the edge-inversion process can permit a racemization of the phosphorus center without decoordination of the phosphine from the metal, see: A. J. Arduengo III, D. A. Dixon, D. C. Roe, J. Am. Chem. Soc. 1986, 108, 6821.
13. A. Brèque, J.-M. Alcaraz, L. Ricard, F. Mathey, New J. Chem. 1989, 12, 369.
14. M.-O. Bevierre, F. Mercier, L. Ricard, F. Mathey, Bull. Soc. Chim. Fr. 1992, 129, 1.
15. S. Otsuka, A. Nakamura, T. Kano, K. Tani, J. Am. Chem. Soc. 1971, 93, 4301.
16. N. Roberts, S. Wild, J. Am. Chem. Soc. 1979, 101, 6254.
17. T. P. Dang, H. B. Kagan, J. Chem. Soc. Chem. Commun. 1971, 481.
18. A. Miyashita, H. Karino, J. Shimamura, T. Chiba, K. Nagano, H. Nohira, H. Takaya, Chem. Lett. 1989, 1849.
19. S.-C. Chan, A. (Monsanto), Eur. Pat. 633 238 A2, June 22, 1990; Chem. Abstr. 1991, 115, 28896.
20. M. Kitamura, T. Okhuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, R. Noyori, J. Am. Chem. Soc. 1988, 110, 629.
21. T. Okhuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995 117, 2675
22. T. Chiba, A. Miyashita, H. Nohira, H. Takaya, Tetrahedron Lett. 1991, 32, 4745.
23. M. Yamaguchi, T. Shima, T. Yamagishi, M. Hida, Tetrahedron Lett. 1990, 31, 5049.
24. A. Miyashita, H. Takaya, T. Souchi, R. Noyori, Tetrahedron 1984, 40, 1245.
25. J. P. Genêt, C. Pinel, V. Ratovelomanana-Vidal, S. Mallart, X. Pfister, L. Bischoff, M. C. Cano de Andrade, S. Darses, C. Galopin, J. A. Laffitte, Tetrahedron: Asymmetry 1994, 5, 675.
26. Beilstein Handbuch der Organische Chemie 6 (1), 235.
27. J. M. Brown, D. I. Hulmes, P. J. Guiry, Tetrahedron 1994, 50, 4493.
28. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-100 103. Copies of the data can be obtained free of charge on application to The Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (Fax: Int. code +(1223)336-033; e-mail: deposit@chemcrys.cam.ac.uk).