Planar chiral 2-ferrocenyloxazolines and 1,1′-bis(oxazolinyl)ferrocenes - Syntheses and applications in asymmetric catalysis

Tetrahedron Asymmetry

Volumn 14, Issue 16, 2003, Pages 2297-2325

  Sutcliffe, Oliver B ^a,b   Bryce, Martin R ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

^b University of Bath   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE; HYDROXYACID; NITROGEN DERIVATIVE; OXAZOLINE DERIVATIVE; PHOSPHORUS DERIVATIVE;

ASYMMETRIC CATALYSIS; ASYMMETRIC SYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; POTENTIOMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; REVIEW; X RAY CRYSTALLOGRAPHY;

EID: 0042164695     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00520-2     Document Type: Review

References (96)

1. Ferrocenes. Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A.; Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995.
2. Shvekhgeimer M.-G.A. Russ. Chem. Rev. 65:1996;41.
3. Kagan H.B., Riant O. Adv. Asymm. Synth. 2:1997;189.
4. Richards C.J., Locke A.J. Tetrahedron: Asymmetry. 9:1998;2377.
5. Togni A. Togni A., Halterman R.L. New Chiral Ferrocenyl Ligands for Asymmetric Catalysis in Metallocenes. Synthesis, Reactivity, Applications. 2:1998;685-721 VCH, Weinheim, Germany.
6. Schmitt G., Klein P., Ebertz W. J. Organomet. Chem. 234:1982;63.
7. DE3127609; Chem. Abstr. 1983, 98, 179359.
8. Nishibayashi Y., Uemura S. Synlett. 1995;79.
9. Nishibayashi Y., Segawa K., Ohe K., Uemura S. Organometallics. 14:1995;5486.
10. Nishibayashi Y., Segawa K., Arikawa Y., Ohe K., Hidai M., Uemura S. J. Organomet. Chem. 545-546:1997;381.
11. Richards C.J., Damalidis T., Hibbs D.E., Hursthouse M.B. Synlett. 1995;74.
12. Richards C.J., Mulvaney A.W. Tetrahedron: Asymmetry. 7:1996;1419.
13. Sammakia T., Latham H.A., Schaad D.R. J. Org. Chem. 60:1995;10.
14. Sammakia T., Latham H.A. J. Org. Chem. 60:1995;6002.
15. Sammakia T., Latham H.A. J. Org. Chem. 61:1996;1629.
16. Vorbruggen H., Krolokliewicz K. Tetrahedron Lett. 22:1981;4471.
17. Basha A., Lipton M., Weinreb S.M. Tetrahedron Lett. 18:1977;4171.
18. Ahn K.H., Cho C.-W., Baek H.-H., Park J., Lee S. J. Org. Chem. 61:1996;4937.
19. Park J., Lee S., Ahn K.H., Cho C.-W. Tetrahedron Lett. 36:1995;7263.
20. Park J., Lee S., Ahn K.H., Cho C.-W. Tetrahedron Lett. 37:1995;6137.
21. Kim S.-G., Cho C.-W., Ahn K.H. Tetrahedron: Asymmetry. 8:1997;1023.
22. Ahn K.H., Cho C.-W., Park J., Lee S. Tetrahedron: Asymmetry. 8:1997;1179.
23. Park J., Quan Z., Lee S., Ahn K.H., Cho C.-W. J. Organomet. Chem. 584:1999;140.
24. Chesney A., Bryce M.R., Chubb R.W.J., Batsanov A.S., Howard J.A.K. Synthesis. 1998;413.
25. Manoury E., Fossey J.S., Aït-Haddou H., Daran J.-C., Balavoine G.G.A. Organometallics. 19:2000;3736.
26. Drahonovsky D., Císarová I., Stepnicka P., Dvoráková H., Malon P., Dvorák D. Collect. Czech. Chem. Commun. 66:2001;588.
27. Zhang W., Adachi Y., Hirao T., Ikeda I. Tetrahedron: Asymmetry. 7:1996;451.
28. Denmark S.E., Nakajima N., Nicaise O.J.-C., Faucher A.-M., Edwards J.P. J. Org. Chem. 60:1995;4884.
29. Sutcliffe, O. B.; Bryce, M. R., unpublished results.
30. Chesney A., Bryce M.R., Chubb R.W.J., Batsanov A.S., Howard J.A.K. Tetrahedron: Asymmetry. 8:1997;2337.
31. Zhang W., Yoneda Y.-I., Kida T., Nakatsuji Y., Ikeda I. Tetrahedron: Asymmetry. 9:1998;3371.
32. Deng W.-P., Hou X.-L., Dai L.-X. Tetrahedron: Asymmetry. 10:1999;4689.
33. Zhang W., Yoshinaga H., Imai Y., Kida T., Nakatsuji Y., Ikeda I. Synlett. 2000;1512.
34. Imai Y., Zhang W., Kida T., Nakatsuji Y., Ikeda I. Chem. Lett. 1999;243.
35. Zhang W., Hirao T., Ikeda I. Tetrahedron Lett. 37:1996;4545.
36. Zhang W., Adachi Y., Hirao T., Ikeda I. Tetrahedron: Asymmetry. 7:1996;1235.
37. Zhang W., Kida T., Nakatsuji Y., Ikeda I. Tetrahedron Lett. 37:1996;7995.
38. Zhang W., Shimanuki T., Kida T., Nakatsuji Y., Ikeda I. J. Org. Chem. 64:1999;6247.
39. Locke A.J., Pickett T.E., Richards C.J. Synlett. 2001;141.
40. Lee S., Koh J.H., Park J. J. Organomet. Chem. 637-639:2001;99.
41. Cho Y.-J., Carroll M.A., White A.J.P., Widdowson D.A., Williams D.J. Tetrahedron Lett. 40:1999;8265.
42. Kim S.-G., Cho C.-W., Ahn K.H. Tetrahedron. 55:1999;10079.
43. Pickett T.E., Richards C.J. Tetrahedron: Asymmetry. 10:1999;4095.
44. Salter R., Pickett T.E., Richards C.J. Tetrahedron: Asymmetry. 9:1998;4239.
45. Bolm C., Muñiz-Fernández K., Seger A., Raabe G., Günther K. J. Org. Chem. 63:1998;7860.
46. Kuwano R., Uemura T., Saitoh M., Ito Y. Tetrahedron Lett. 40:1999;1327.
47. You S.-L., Hou X.-L., Dai L.-X., Cao B.-X., Sun J. Chem. Commun. 2000;1933.
48. Pickett T.E., Richards C.J. Tetrahedron Lett. 42:2001;3767.
49. You S.-L., Luo Y.-M., Deng W.-P., Hou X.-L., Dai L.-X. J. Organomet. Chem. 637-639:2001;845.
50. You S.-L., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W. J. Org. Chem. 67:2002;4684.
51. Solladie G., Hugele P., Bartch R. J. Org. Chem. 63:1998;3895.
52. Sebesta R., Toma S., Salisová M. Eur. J. Org. Chem. 2002;692.
53. Richards C.J., Hibbs D.E., Hursthouse M.B. Tetrahedron Lett. 36:1995;3745.
54. Strangeland E.L., Sammakia T. Tetrahedron. 53:1997;16503.
55. Deng W.-P., Hou X.-L., Dai L.-X., Yu Y.-H., Xia W. Chem. Commun. 2000;285.
56. Dai L.-X., Hou X.-L., Deng W.P., You S.-L., Zhou Y.-G. Pure Appl. Chem. 71:1999;1401.
57. Shintani R., Lo M.M.-C., Fu G.C. Org. Lett. 2:2000;3695.
58. Ahn K.H., Cho C.-W., Park J., Lee S. Bull. Korean Chem. Soc. 18:1997;789.
59. Malone Y.M., Guiry P.J. J. Organomet. Chem. 603:2000;110.
60. Chung K.-G., Miyake Y., Uemura S. J. Chem. Soc., Perkin Trans. 1. 2000;2725.
61. Chung K.-G., Miyake Y., Uemura S. J. Chem. Soc., Perkin Trans. 1. 2000;15.
62. Hennessy A.J., Malone Y.M., Guiry P.J. Tetrahedron Lett. 40:1999;9163.
63. Deng W.-P., Hou X.-L., Dai L.-X., Dong X.-W. Chem. Commun. 2000;1483.
64. Nishibayashi Y., Segawa K., Takada H., Ohe K., Uemura S. Chem. Commun. 1996;847.
65. Nishibayashi Y., Takei I., Uemura S., Hidai M. Organometallics. 17:1998;3420.
66. Takei I., Nishibayashi Y., Arikawa Y., Uemura S., Hidai M. Organometallics. 18:1999;2271.
67. Takei I., Nishibayashi Y., Ishii Y., Mizobe Y., Uemura S., Hidai M. Chem. Commun. 2001;2360.
68. Gimeno J., Lastra E., Madrigal C., Graiff C., Tiripicchio A. J. Organomet. Chem. 637-639:2001;463.
69. Sammakia T., Strangeland E.L. J. Org. Chem. 62:1997;6104.
70. Du X.-D., Dai L.-X., Hou X.-L., Xia L.-J., Tang M.-H. Chin. J. Chem. 16:1998;90.
71. Nishibayashi Y., Takei I., Uemura S., Hidai M. Organometallics. 18:1999;2291.
72. Fukuzawa S.-I., Kato H. Synlett. 1998;727.
73. Bolm C., Muñiz-Fernández K., Seger A., Raabe G. Synlett. 1997;1051.
74. Bolm C., Muñiz K., Hildebrand J.P. Org. Lett. 1:1999;491.
75. Deng W.-P., Hou X.-L., Dai L.-X. Tetrahedron: Asymmetry. 10:1999;4689.
76. Bolm C., Muñiz K. Chem. Commun. 1999;1295.
77. Bolm C., Hermanns N., Hildebrand J.P., Muñiz K. Angew. Chem., Int. Ed. 39:2000;3465.
78. Bolm C., Hermanns N., Kesselgruber M., Hildebrand J.P. J. Organomet. Chem. 624:2001;157.
79. Bolm C., Hermanns N., Claßen A., Muñiz K. Bioorg. Med. Chem. Lett. 12:2002;1795.
80. You S.-L., Zhou Y.-G., Hou X.-L., Dai L.-X. Chem. Commun. 1998;2765.
81. Allen J.V., Coote S., Dawson G.J., Frost C.G., Martin C.J., Williams J.M.J. J. Chem. Soc., Perkin Trans. 1. 1994;2065.
82. Karlström A.S.E., Huerta F.F., Meuzelaar G.J., Bäckvall J.-E. Synlett. 2001;923.
83. You S.-L., Hou X.-L., Dai L.-X. Tetrahedron: Asymmetry. 11:2000;1495.
84. Leutenegger V., Umbricht G., Fahrini C., von Matt P., Pfaltz A. Tetrahedron. 48:1992;2143.
85. Fukuzawa S.-I., Takahashi K., Kato H., Yamazaki H. J. Org. Chem. 62:1997;7711.
86. Bolm C., Kesselgruber M., Grenz A., Nermanns N., Hildebrand J.P. New. J. Chem. 25:2001;13.
87. Wirth T. Tetrahedron Lett. 36:1995;7849.
88. Wirth T., Kulicke K.J., Fragale G. Helv. Chim. Acta. 79:1996;1957.
89. Santi C., Wirth T. Tetrahedron: Asymmetry. 10:1999;1019.
90. Donde Y., Overman L.E. J. Am. Chem. Soc. 121:1999;2933.
91. Warshawsky A.M., Meyers A.I. J. Am. Chem. Soc. 112:1990;8090.
92. Nelson T.D., Meyers A.I. J. Org. Chem. 59:1994;2655.
93. Kaifer A.E., Mendoza S. Gokel G. Comprehensive Supramolecular Chemistry. 1:1996;701 Pergamon, Oxford.
94. Chesney A., Bryce M.R., Batsanov A.S., Howard J.A.K., Goldenberg L.M. Chem. Commun. 1998;677.
95. Sutcliffe O.B., Chesney A., Bryce M.R. J. Organomet. Chem. 637-639:2001;134.
96. Pericas M.A., Purgjaner C., Riera A., Vidal-Ferran A., Gómez M., Jiménez F., Muller G., Rocamora M. Chem. Eur. J. 8:2002;4164. and references cited therein.