Synthesis of novel chiral phosphinocyrhetrenyloxazoline ligands and their application in asymmetric catalysis

Organic and Biomolecular Chemistry

Volumn 1, Issue 1, 2003, Pages 145-152

  Bolm, Carsten ^a   Xiao, Li ^a   Kesselgruber, Martin ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; AMINATION; CATALYST ACTIVITY; HYDROGEN BONDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ASSYMETRIC CATALYSIS; ASSYMETRIC HYDROSILYLATION; LEWIS BASICITY; PHOSPHINE SELENIDES; PHOSPHINOCYRHETRENYLLOXAZOLINE;

AMINES;

EID: 0041823394     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b208345k     Document Type: Article

References (52)

1. (a) Transition Metals in Organic Synthesis, eds. M. Beller and C. Bolm. Wiley-VCH. Weinheim. 1998
2. (b) Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin. 1999
3. (c) Catalytic Asymmetric Synthesis, ed. I. Ojima, Wiley-VCH, New York, 2000.
4. (a) Ferrocenes, eds. A. Togni and T. Hayashi, VCH, Weinheim. 1995
5. (b) A. Togni, Chimia, 1996, 50, 86
6. (c) A. Togni, Angew. Chem., 1996, 108, 1581 (Angew. Chem., Int. Ed. Engl., 1996, 35, 1475)
7. (d) H.-U. Blaser, H.-P. Buser, K. Coers, R. Hanreich, H.-P. Jalett, E. Jelsch, B. Pugin, H.-D. Schneider, F. Spindler, and A. Wegmann, Chimia, 1999, 53, 275
8. (e) T. Sturm, L. Xiao and W. Weissensteiner, Chimia, 2001, 55, 688.
9. (a) C. Bolm and K. Muniz, Chem. Commun., 1999, 1295
10. (b) C. Bolm, N. Hermanns, J. P. Hildebrand and K. Muniz, Angew. Chem., 2000, 112, 3609 (Angew. Chem., Int. Ed., 2000, 39, 3465).
11. (c) C. Bolm, M. Kesselgruber, N. Hermanns, J. P. Hildebrand and G. Raabe, Angew. Chem., 2001, 113. 1536 (Angew. Chem. Int. Ed. 2001, 40, 1488).
12. (a) C. J. Richards, T. Damalidis, D. E. Hibbs and M. B. Hursthouse, Synlett, 1995, 74
13. (b) T. Sammakia, H. A. Latham and D. R. Schaad, J. Org. Chem., 1995, 60, 10
14. (c) Y. Nishibayashi and S. Uemura, Synlett, 1995, 79.
15. (a) C. J. Richards and A. W. Mulvaney, Tetrahedron: Asymmetry, 1996, 7, 1419
16. (b) K. H. Ahn, C.-W. Cho, H.-H. Beak, J. Park and S. Lee, J. Org. Chem., 1996, 61, 4937.
17. (a) K. H. Ahn, C.-W. Cho, J. Park and S. Lee, Tetrahedron: Asymmetry, 1997, 8, 1179
18. (b) S.-L. You, X.-L. Hou, L.-X. Dai, Y.-H. Yu and W. Xia, J. Org. Chem., 2002, 67, 4684.
19. (a) A. J. Hennessy, Y. M. Malone and P. J. Guiry, Tetrahedron Lett., 1999, 40, 9163
20. (b) W.-P. Deng, X.-L. Hou, L.-X. Dai and X.-W. Dong, Chem. Commun., 2000, 1483.
21. (a) T. Sammakia and E. L. Stangeland, J. Org. Chem., 1997, 62. 6104
22. (b) Y. Nishibayashi, I. Takei, S. Uemura and M. Hidai, Organometallics, 1999, 18, 2291.
23. (a) Y. Nishibayashi, K. Segawa, K. Ohe and S. Uemura, Organometallics, 1995, 14, 5486
24. (a) Y. Nishibayashi, I. Takei, S. Uemura and M. Hidai, Organometallics, 1998, 17, 3420
25. (c) I. Takei, Y. Nishibayashi, Y. Arikawa, S. Uemura and M. Hidai, Organometallics, 1999, 18, 2271
26. (d) I. Takei, Y. Nishibayashi, Y. Mizobe, S. Uemura and M. Hidai, Chem. Commun., 2001, 2360.
27. C. Bolm and M. Kesselgruber, DE 100 40 017.5, 2000.
28. D. A. Evans, G. S. Peterson, J. S. Johnson, D. M. Barnes, K. R. Campos and K. A. Woerpel, J. Org. Chem., 1998, 63, 4541.
29. (a) G. Consiglio and R. M. Waymouth, Chem. Rev., 1989, 89, 257
30. (b) C. D. Frost, J. Howarth and J. M. J. Williams, Tetrahedron, 1992, 3, 1089
31. (c) B. M. Trost and D. L. Van Vranken, Chem. Rev., 1996, 96, 395
32. (d) B. M. Trost, Acc. Chem. Res., 1996, 29, 355
33. (e) A. Pfaltz and M. Lautens, Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin. 1999, ch. 24, p. 833.
34. (a) G. Zassinovich, G. Mestroni and S. Gladiali, Chem. Rev., 1992, 92, 1051
35. (b) R. Noyori and S. Hashiguchi, Acc. Chem. Res., 1997, 30, 97
36. (c) M. J. Palmer and M. Wills, Tetrahedron: Asymmetry, 1999, 10, 2045
37. (d) M. Wills, M. Palmer, A. Smith, J. Kenny and T. Walsgrove, Molecules, 2000, 5, 4
38. (e) R. Noyori, M. Yamakawa and S. Hashiguchi, J. Org. Chem., 2001, 66, 7931.
39. (a) H. Nishiyama and K. Itoh, Transition Metals in Organic Synthesis, eds. M. Beller and C. Bolm, Wiley-VCH, Weinheim, 1998, ch. 2, p. 111
40. (b) H. Nishiyama, Comprehensive Asymmetric Catalysis, eds. E. N. Jacobsen, A. Pfaltz and H. Yamamoto, Springer, Berlin, 1999, ch. 6.3 p. 267.
41. (a) L.-X. Dai, X.-L. Hou, W.-P. Deng, S.L. You and Y.-G. Zhou, Pure Appl. Chem., 1999, 71, 1401
42. (b) W.-P. Deng, X.-L. Hou, L.-X. Dai, Y.-H. Yu and W. Xia, Chem. Commun., 2000, 285
43. (c) W.-P. Deng, S.-L. You, X.-L. Hou, L.-X. Dai, Y.-H. Yu, W. Xia, and J. Sun, J. Am. Chem. Soc., 2001, 123, 6508.
44. (a) D. W. Allen and B. F. Taylor, J. Chem. Res. (S), 1981, 220
45. (b) D. W. Allen and B. F. Taylor, J. Chem. Soc., Dalton Trans., 1982, 51
46. (c) D. W. Allen, L. A. March and I. W. Nowell, J. Chem. Soc., Dalton Trans., 1984, 483
47. (d) D. W. Allen and I. W. Nowell, J. Chem. Soc., Dalton Trans., 1985, 2505
48. (e) D. W. Allen and B. F. Taylor, J. Chem. Res. (S), 1986, 392.
49. J. Sprinz and G. Helmchen, Tetrahedron Lett., 1993, 34, 1769.
50. P. von Matt and A. Pfaltz, Angew. Chem., 1993, 105, 614 (Angew. Chem., Int. Ed. Engl., 1993, 32, 566).
51. P. Sennhenn, B. Gabler and G. Helmchen, Tetrahedron Lett., 1994, 35, 8595.
52. T. Hayashi, A. Yamamoto, Y. Ito, E. Nishioka, H. Muira and K. Yanagi, J. Am. Chem. Soc., 1989, 111, 6301.