SYNPHOS: A new atropisomeric diphosphine ligand. From laboratory-scale synthesis to scale-up development

Organic Process Research and Development

Volumn 7, Issue 3, 2003, Pages 399-406

  Duprat De Paule, Sébastien ^a   Jeulin, Séverine ^a   Ratovelomanana Vidal, Virginie ^a   Genêt, Jean Pierre ^a   Champion, Nicolas ^b   Deschaux, Gilles ^b   Dellis, Philippe ^b  

^a PSL RESEARCH UNIVERSITY   (France)

^b SYNKEM SAS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

[(5,6),(5',6')BIS(ETHYLENEDIOXY)BIPHENYL 2,2' DIYL]BIS(DIPHENYLPHOSPHINE); LIGAND; PHOSPHINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; HYDROGENATION; ISOMER; LABORATORY; SCALE UP; SYNTHESIS;

EID: 0038722880     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op034016w     Document Type: Article

References (28)

1. (a) Kagan, H. B. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999; Vol. I, Chapter 2, p 9.
2. (b) Ojima, I. Catalytic Asymmetric Synthesis; John Wiley and Sons: New York, 2000.
3. (a) Miyashita, A.; Yasuda A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.
4. (b) Noyori, R.; Takaya, H. Acc. Chem. Res. 1990, 23, 345.
5. (a) Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
6. (b) Schmid, R.; Broger, E. A.; Cereghetti, M.; Crameri, Y.; Foricher, J.; Lalonde, M.; Müller, R. K.; Scalone, M.; Schoettel, G.; Zutter U. Pure Appl. Chem. 1996, 68, 131.
7. (a) Saito, Sayo, T. N.; Xiaoyaong, Z.; Yokozawa, T. (Takasago International Corporation). EP 0850945, 1998.
8. (b) Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; T. Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
9. Duprat de Paule, S.; Champion, N.; Vidal, V.; Genêt, J.-P.; Dellis, P. French Patent 0112499; PCT FR02/03146.
10. Pai, C. C.; Li, Y. M.; Zhou, Z. Y.; Chan, A. S. C. Tetrahedron Lett. 2002, 43, 2789.
11. Duprat de Paule, S.; Jeulin, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Tetrahedron Lett. 2003, 44, 823.
12. Brown, J. M.; Woodward, S. C. J. Org. Chem. 1991, 56, 6803.
13. Brunner, H.; Pieronczyk, W.; Schönhammer, B.; Streng, K.; Bernal, I.; Korp J. Chem. Ber. 1981, 114, 1137.
14. (a) Ranade, A. C. Jayalakshmi S. Chem. Ind. 1978, 234.
15. (b) Mattson, R. J.; Sloan, C. P.; Lockart, C. C.; Catt, J. D.; Gao, Q.; Huang, S. J. Org. Chem. 1999, 64, 8004.
16. (a) Laue, C.; Schröder, G.; Arlt, D. U.S. Patent 5,710,339, 1998.
17. (b) Foricher, J.; Schmid, R. EP 0926152 A1, 1998.
18. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
19. (b) Noyori, R. Tetrahedron 1994, 50, 4259.
20. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis: Ojima, I., Ed.; 2000; pp 1-110.
21. (d) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
22. (e) Noyori, R. Angew. Chem., Int. Ed. 2002, 41, 2008.
23. (f) Ratovelomanana-Vidal, V.; Genêt, J.-P. J. Organomet. Chem. 1998, 567, 163.
24. (g) Genêt, J.-P. Pure Appl. Chem. 2002, 74, 77.
25. (a) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Cano de Andrade, M. C.; Laffitte, J.-A. Tetrahedron: Asymmetry 1994, 5, 665.
26. (b) Genêt, J.-P.; Pinel, C.; Ratovelomanana-Vidal, V.; Mallart, S.; Pfister, X.; Bischoff, L.; Cano de Andrade, M. C.; Darses, S.; Galopin, C.; Laffitte J.-A. Tetrahedron: Asymmetry 1994, 5, 675.
27. (c) Genêt, J.-P. Reductions in Organic Synthesis; ACS Symposium Series 641; American Chemical Society: Washington, DC, 1996; pp 31-51.
28. Blanc, D.; Ratovelomanana-Vidal, V.; Gillet, J.-P.; Genêt J.-P. J. Organomet. Chem 2000, 603, 128.