New efficient synthesis of Taniaphos ligands: Application in ruthenium- and rhodium-catalyzed enantioselective hydrogenations

Tetrahedron Asymmetry

Volumn 15, Issue 1, 2004, Pages 91-102

  Tappe, Katja ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

Enantioselective hydrogenation; Ferrocene ligands

Indexed keywords

1,5 DIPHOSPHINE FERROCENE; FERROCENE DERIVATIVE; LIGAND; RHODIUM; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROGENATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0347418206     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.11.004     Document Type: Article

References (41)

1. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley, New York.
2. (a) Fryzuk M.D., Bosnich B. J. Am. Chem. Soc. 99:1977;6262;
3. (b) Knowles W.S. Acc. Chem. Res. 16:1983;106;
4. (c) Noyori R., Takaya H. Acc. Chem. Res. 23:1990;345;
5. (d) Burk M.J., Feaster J.E., Nugent W.A., Harlow R.L. J. Am. Chem. Soc. 115:1993;10125;
6. (e) Togni A., Breutel C., Schnyder A., Spindler F., Landert H., Tijani T. J. Am. Chem. Soc. 116:1994;4062;
7. (f) Sturm T., Weissensteiner W., Spindler F. Adv. Synth. Catal. 345:2003;160.
8. (a) Ireland T., Grossheimann G., Wieser-Jeunesse C., Knochel P. Angew. Chem. 111:1999;3397 Angew. Chem., Int. Ed. 38:1999;3212;
9. (a) Ireland T., Grossheimann G., Wieser-Jeunesse C., Knochel P. Angew. Chem. 111:1999;3397 Angew. Chem., Int. Ed. 38:1999;3212;
10. (b) Ireland T., Tappe K., Grossheimann G., Knochel P. Chem. Eur. J. 8:2002;843.
11. Muñiz K., Bolm C. Chem. Eur. J. 6:2000;2309.
12. Lotz M., Polborn K., Knochel P. Angew. Chem. 114:2002;4902 Angew. Chem., Int. Ed. 41:2002;4708.
13. Lotz M., Polborn K., Knochel P. Angew. Chem. 114:2002;4902 Angew. Chem., Int. Ed. 41:2002;4708.
14. Kagan H.B., Diter P., Gref A., Guillaneux D., Masson-Szymczak A., Rebière F., Riant O., Samuel O., Taudien S. Pure Appl. Chem. 68:1996;29.
15. Rausch M., Vogel M., Rosenberg H. J. Org. Chem. 22:1957;903.
16. Mathre D.J., Jones T.K., Xavier L.C., Blacklock T.J., Reamer R.A., Mohan J.J., Turner Jones E.T., Hoogsteen K., Baum M.W., Grabowski E.J.J. J. Org. Chem. 56:1991;751.
17. (a) Corey E.J., Bakshi R.K., Shibata S. J. Am. Chem. Soc. 109:1987;5551
18. (b) Wright J., Framber P., Reeves P. J. Organomet. Chem. 476:1994;215.
19. Ugi I.K., Marquarding D., Gokel G.W. J. Org. Chem. 37:1972;3052.
20. Ugi I.K., Batelle L.F., Bau R., Gokel G.W. J. Am. Chem. Soc. 95:1973;482.
21. Lotz M., Ireland T., Almena Perea J.J., Knochel P. Tetrahedron: Asymmetry. 10:1999;1839.
22. (a). For reviews, see: Koenig K.E. Asymmetric Synthesis. 1985;Academic Press, Orlando, FL. p 71 (b) Takaya H., Ohta T., Noyori R. Catalytic Asymmetric Synthesis. 1993;VCH, New York. p 1 (c) Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley, New York. p 16.
23. (a). For reviews, see: Koenig K.E. Asymmetric Synthesis. 1985;Academic Press, Orlando, FL. p 71 (b) Takaya H., Ohta T., Noyori R. Catalytic Asymmetric Synthesis. 1993;VCH, New York. p 1 (c) Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley, New York. p 16.
24. (a). For reviews, see: Koenig K.E. Asymmetric Synthesis. 1985;Academic Press, Orlando, FL. p 71 (b) Takaya H., Ohta T., Noyori R. Catalytic Asymmetric Synthesis. 1993;VCH, New York. p 1 (c) Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;John Wiley, New York. p 16.
25. (a) Genêt J.P., Pinel C., Mallart S., Jugé S., Thorimbert S., Laffitte J. Tetrahedron: Asymmetry. 2:1991;555
26. Genêt J.P., Pinel C., Ratovelomanana-Vidal V., Mallart S., Pfister X., Bischoff L., Darses S., Galopin C., Laffitte J.A. Tetrahedron: Asymmetry. 5:1994;675.
27. (a) RajanBabu T.V., Ayers T.A., Casalnuovo A.L. J. Am. Chem. Soc. 116:1994;4101
28. (b) Landis C.R., Halpern J. J. Am. Chem. Soc. 109:1987;1746
29. (c) Knowles W.S. Acc. Chem. Res. 16:1983;106
30. (d) Chan A.S.C., Pluth J.J., Halpern J. J. Am. Chem. Soc. 102:1980;5952
31. (e) Brown J.M. Chem. Soc. Rev. 1993;25
32. (f) Burk M.J., Feaster J.E., Nugent W.A., Harlow R.L. J. Am. Chem. Soc. 115:1993;10125.
33. For a recent review, see: Kobayashi S., Ishitani H. Chem. Rev. 99:1999;1069.
34. (a) Burk M.J., Feaster J.E. J. Am. Chem. Soc. 114:1992;6266;
35. (b) Burk M.J., Martinez J.P. Tetrahedron. 50:1994;4399.
36. Ireland, T. Dissertation, Marburg, 2000.
37. Jary W.G., Mahler A.-K., Purkathofer T., Baumgartner J. J. Organomet. Chem. 629:2001;208.
38. Caroll M.A., White A.J.P., Widdowson D.A., Williams D.J. J. Chem. Soc., Perkin Trans. 1. 2000;1551.
39. Marquarding D., Klusacek H., Gokel G., Hoffmann P., Ugi I. J. Am. Chem. Soc. 92:1970;5389.
40. Almena Perea J.J., Börner A., Knochel P. Tetrahedron Lett. 39:1998;8073. and references cited therein.
41. Mashima K., Kusano K.H., Sato N., Matsumura Y., Nozaki K., Kumobayashi H., Sayo N., Hori Y., Ishizaki T., Akutagawa S., Takaya H. J. Org. Chem. 59:1994;3064.