Synthesis of JOSIPHOS-type ligands via a diastereoselective three-component reaction and their application in asymmetric rhodium-catalyzed hydroborations

Tetrahedron Asymmetry

Volumn 16, Issue 20, 2005, Pages 3385-3393

  Yasuike, Shuji ^a   Kofink, Christiane C ^a   Kloetzing, Ralf J ^a   Gommermann, Nina ^a   Tappe, Katja ^a   Gavryushin, Andrei ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FERROCENE DERIVATIVE; JOSIPHOS; LIGAND; PHOSPHINE DERIVATIVE; RHODIUM; STYRENE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; DIASTEREOISOMER; HYDROBORATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 27644533318     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.08.051     Document Type: Article

References (44)

1. R. Noyori Asymmetric Catalysis in Organic Synthesis 1994 John Wiley & Sons New York
2. A. Togni, and T. Hayashi Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Material Science 1995 VCH Weinheim
3. M. Perseghini, and A. Togni Sci. Synth. 1 2002 889
4. For recent reviews see: R.C.J. Atkinson, V.C. Gibson, and N.J. Long Chem. Soc. Rev. 33 2004 313
5. T.J. Colacot Chem. Rev. 103 2003 3101
6. for further examples see: T. Sturm, W. Weissensteiner, and F. Spindler Adv. Synth. Catal. 345 2003 160
7. T. Ireland, G. Grossheimann, C. Wieser-Jeunesse, and P. Knochel Angew. Chem., Int. Ed. 38 1999 3212
8. M. Lotz, K. Polborn, and P. Knochel Angew. Chem., Int. Ed. 41 2002 4708
9. M. Lotz, G. Kramer, and P. Knochel Chem. Commun. 2002 2546
10. J.J. Almena Perea, M. Lotz, and P. Knochel Tetrahedron: Asymmetry 10 1999 375
11. D. Enders, R. Peters, R. Lochtman, G. Raabe, J. Runsink, and J.W. Bats Eur. J. Org. Chem. 2002 3399
12. U. Berens, M.J. Burk, A. Gerlach, and W. Hems Angew. Chem., Int. Ed. 39 2000 1981
13. G.W. Gokel, D. Marquarding, and I.K. Ugi J. Org. Chem. 37 1972 3052
14. G. Gokel, P. Hoffmann, H. Klusacek, D. Marquarding, and I. Ugi Angew. Chem. 82 1970 77
15. T. Hayashi, T. Mise, S. Mitachi, K. Yamamoto, and M. Kumada Tetrahedron Lett. 17 1976 1133
16. A. Togni, C. Breutel, A. Schnyder, F. Spindler, H. Landert, and A. Tijani J. Am. Chem. Soc. 116 1994 4062
17. A. Togni Angew. Chem. 108 1996 1581
18. A. Togni, N. Bieler, U. Burckhardt, C. Köllner, G. Pioda, R. Schneider, and A. Schnyder Pure Appl. Chem. 71 1999 1531
19. J. McGarrity, F. Spindler, R. Fuchs, M. Eyer (Lonza AG), EP-A624587A2, 1995.
20. F. Spindler, B. Pugin, H.-P. Jalett, H.-P. Buser, U. Pittelkow, and H.U. Blaser (Novartis AG) Chem. Ind. (Dekker) 68 1996 153
21. F. López, S.R. Harutyunyan, A. Meetsma, A.J. Minaard, and B.L. Feringa Angew. Chem., Int. Ed. 44 2005 2752
22. B.H. Lipshutz, J.M. Servesko, and B.R. Taft J. Am. Chem. Soc. 126 2004 8352
23. B.H. Lipshutz, and J.M. Servesko Angew. Chem., Int. Ed. 42 2003 4789
24. N. Gommermann, C. Koradin, K. Polborn, and P. Knochel Angew. Chem., Int. Ed. 42 2003 5763
25. H. Dube, N. Gommermann, and P. Knochel Synthesis 2004 2015
26. N. Gommermann, and P. Knochel Chem. Commun. 2004 2324
27. T. Hayashi, T. Mise, M. Fukushima, M. Kagotani, N. Nagashima, Y. Hamada, A. Matsumoto, S. Kawakami, and M. Konishi Bull. Chem. Soc. Jpn. 53 1980 1138
28. E.J. Corey, and A.W. Gross Tetrahedron Lett. 25 1984 495
29. K. Tappe, and P. Knochel Tetrahedron: Asymmetry 15 2004 91
30. D. Marquarding, H. Klusacek, G. Gokel, P. Hoffmann, and I. Ugi J. Am. Chem. Soc. 92 1970 5389
31. A. Ohno, M. Yamane, and T. Hayashi Tetrahedron: Asymmetry 6 1995 2495
32. P. Pellon Tetrahedron Lett. 33 1992 4451
33. T. Imamoto, T. Kusumoto, N. Suzuki, and K. Sato J. Am. Chem. Soc. 107 1985 5301
34. A. Gavryushin, K. Polborn, and P. Knochel Tetrahedron: Asymmetry 15 2004 2279
35. For general reviews see: A.-M. Carroll, T.P. O'Sullivan, and P.J. Guiry Adv. Synth. Catal. 347 2005 609
36. G. Chelucci, G. Orrù, and G. Pinna Tetrahedron 59 2003 9471
37. I. Beletskaya, and A. Pelter Tetrahedron 53 1997 4957
38. For further examples: T.F. Knöpfel, P. Aschwanden, T. Ichikawa, T. Watanabe, and E.M. Carreira Angew. Chem., Int. Ed. 43 2004 5971
39. A.M. Segarra, C. Claver, and E. Fernandez Chem. Commun. 2004 464
40. F.Y. Kwong, Q. Yang, T.C.W. Mak, A.S.C. Chan, and K.S. Chan J. Org. Chem. 67 2002 2769
41. S. Demay, F. Volant, and P. Knochel Angew. Chem., Int. Ed. 40 2001 1235
42. E. Fernandez, K. Maeda, M.W. Hooper, and J.M. Brown Chem. Eur. J. 6 2000 1840
43. M.T. Reetz, E.W. Beuttenmuller, R. Goddard, and M. Pasto Tetrahedron Lett. 40 1999 4977
44. H. Doucet, E. Fernandez, T.P. Layzell, and J.M. Brown Chem. Eur. J. 5 1999 1320