Enantioselective catalysis: Part 114. Chirostructural analysis of bis(diphenylphosphanyl)ethane transition metal chelates2

Journal of Organometallic Chemistry

Volumn 553, Issue 1-2, 1998, Pages 285-306

  Brunner, Henri ^a   Winter, Andreas ^a   Breu, Josef ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Bis(diphenylphosphanyl)ethane type ligands; Chirality transfer; Conformational analysis; Phenyl ring orientation; Structural analyses

Indexed keywords

EID: 0001115955     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(97)00570-6     Document Type: Article

References (101)

1. H. Brunner, M. Janura, Synthesis, in press.
2. I. Ojima, Catalytic Asymmetric Synthesis, VCH, New York (1993).
3. K.E. Koenig, In: J.D. Morrison (Ed.), Asymmetric Synthesis, Vol. 5, Academic Press, Orlando (1993) p. 71.
4. H. Brunner, M. Muschiol, F. Prester, Angew. Chem., Int. Ed. Engl. 29 (1990) 653. Angew. Chem., Int. Ed. Engl. 29 (1990) 653.
5. H. Brunner, M. Muschiol, F. Prester, Angew. Chem., Int. Ed. Engl. 29 (1990) 653. Angew. Chem., Int. Ed. Engl. 29 (1990) 653.
6. Lautens M., Lautens J.C., Smith A.C. J. Am. Chem. Soc. 112:1990;5627.
7. Knowles W.S., Vineyard B.D., Sabacky M.J., Stults B.R. Fundam. Res. Homogeneous Catal. 3:1978;537.
8. Seebach D., Devaquet E., Ernst A., Hayakawa M., Kühnle F.N.M., Schweizer W.B., Weber B. Helv. Chim. Acta. 78:1995;1636.
9. F. Basolo, R.G. Pearson, Mechanisms of Inorganic Reactions, Wiley, New York (1976) p. 336.
10. Inorg. Chem., 9 (1970) p. 1.
11. The compounds COCONO, DIRE and FP14 were taken from the original literature. Their names are not CSD codes.
12. F. Morandini, G. Consiglio, B. Straub, G.F. Ciani, A. Sironi, J. Chem. Soc., Dalton. Trans. (1983) 2293.
13. Consiglio G., Morandini F., Ciani G.F., Sironi A., Kretschmer M. J. Am. Chem. Soc. 105:1983;1391.
14. A. Dietl, PhD Thesis, University of Regensburg (1994).
15. Consiglio G., Morandini F., Ciani G.F., Sironi A. Organometallics. 5:1986;1976.
16. Morris R.H., Sawyer J.F., Sella A. Acta Crystallogr., C (Cr. Str. Comm.). 44:1988;23.
17. Morandini F., Consiglio G., Sironi A. Gazz. Chim. Ital. 117:1987;61.
18. Morandini F., Pilloni G., Consiglio G., Sironi A., Moret M. Organometallics. 12:1993;3495.
19. M.C.B. Colbert, A.J. Edwards, J. Lewis, N.J. Long, N.A. Page, D.G. Parker, P.R. Raithby, J. Chem. Soc, Dalton Trans. (1994) 2589.
20. Farrar D.H., Payne N.C. J. Am. Chem. Soc. 107:1985;2054.
21. Thorburn I.S., Rettig S.J., James B.R. Inorg. Chem. 25:1986;234.
22. Young C.G., Rettig S.J., James B.R. Can. J. Chem. 64:1986;51.
23. Ball R.G., Payne N.C. Inorg. Chem. 16:1977;1187.
24. Farrugia L.J., McDonald N., Peacock R.D. J. Cluster Sci. 5:1994;341.
25. Brown J.M., Evans P.L., Maddox P.J., Sutton K.H. J. Organomet. Chem. 359:1989;115.
26. Morandini F., Consiglio G., Sironi A., Moret M. J. Organomet. Chem. 370:1989;305.
27. Kyba E.P., Davis R.E., Juri P.N., Shirley K.R. Inorg. Chem. 20:1981;3616.
28. Brunner H., Rahman A.F.M.M., Bernal I. Inorg. Chim. Acta. 83:1984;L93.
29. Halg W.J., Ohrstrom L.R., Ruegger H., Venanzi L.M., Gerfin T., Gramlich V. Helv. Chim. Acta. 76:1993;788.
30. Nishiyama H., Brunner H., Jones P.G. J. Organomet. Chem. 405:1991;247.
31. Davis R.E., Meyer B.B., Hassett K.L., Juri P.N., Kyba E.P. Acta Crystallogr., C (Cr. Str. Comm.). 40:1984;21.
32. Brunner H., Vitulli G., Porzio W., Zocchi M. Inorg. Chim. Acta. 96:1985;67.
33. D.L. Allen, V.C. Gibson, M.L.H. Green, J.F. Skinner, J. Bashkin, P.D. Grebenik, J. Chem. Soc., Chem. Comm. (1983) 895.
34. Fenske D., Christidis A. Z. Naturforsch. B. 38:1983;1295.
35. T. Minami, Y. Okada, R. Nomura, S. Hirota, Y. Nagahara, K. Fukuyama, Chem. Lett. (1986) 613.
36. Cotton F.A., Kang S.J. Inorg. Chim. Acta. 209:1993;23.
37. Nagel U., Rieger B. Chem. Ber. 121:1988;1123.
38. Cotton F.A., DeCanio E.C., Kibala P.A., Vidyasagar K. Inorg. Chim. Acta. 184:1991;221.
39. Saito K., Saijo S., Kotera K., Date T. Chem. Pharm. Bull. 33:1985;1342.
40. H. Brunner, P. Faustmann, publication in preparation.
41. Bruce M.I., Cifuentes M.P., Humphrey M.G., Poczman E., Snow M.R., Tiekink E.R.T. J. Organomet. Chem. 338:1988;237.
42. J.L. Bookham, W. McFarlane, M. Thornton-Pett, S. Jones, J. Chem. Soc., Dalton Trans. (1990) 3621.
43. Adams R.D., Davidson A., Selegue J.P. J. Am. Chem. Soc. 101:1979;7232.
44. Oliver J.D., Riley D.P. Organometallics. 2:1983;1032.
45. Saare A., Dahlenburg L. Z. Naturforsch. B. 47:1992;247.
46. Chung-Yuan Liu, Ming-Chu Cheng, Shie-Ming Peng, Shiuh-Tzung Liu, Organometallics, 13 (1994) 4294.
47. Brunner H., Hammer B., Krüger C., Angermund K., Bernal I. Organometallics. 4:1985;1063.
48. Slack D.A., Greveling I., Baird M.C. Inorg. Chem. 18:1979;3125.
49. H.B. Kagan, Comprehensive Organometallic Chemistry, Vol. 8, In: G. Wilkinson, F.G.A. Stone, E.W. Abel (Eds.), Pergamon, Oxford (1982) p. 463.
50. H. Brunner, Angew. Chem. 95 (1983) 921. Angew Chem. Int. Ed. Engl. 22 (1983) 897.
51. H. Brunner, Angew. Chem. 95 (1983) 921. Angew Chem. Int. Ed. Engl. 22 (1983) 897.
52. R.O. Gould, T.A. Stephenson, M.A. Thomson, J. Chem. Soc., Dalton Trans. (1981) 2508.
53. Fultz W.C., Rheingold A.L., Kreter P.E., Meek D.W. Inorg. Chem. 22:1983;860.
54. G. Smith, D.J. Cole-Hamilton, M. Thornton-Pett, M.B. Hursthouse, J. Chem. Soc., Dalton Trans. (1983) 2501.
55. Ball R.G., Edelmann F., Kiel G.-Y., Takats J., Drews R. Organometallics. 5:1986;829.
56. Lehner H., Matt D., Togni A., Thouvenot R., Venanzi L.M., Albinati A. Inorg. Chem. 23:1984;4254.
57. Bruce M.I., Hambley T.W., Snow M.R., Swincer A.G. Organometallics. 4:1985;501.
58. G.J. Baird, S.G. Davies, S.D. Moon, S.J. Simpson, R.H. Jones, J. Chem. Soc., Dalton Trans. (1985) 1479.
59. Bruce M.I., Dean C., Duffy D.N., Humphrey M.G., Koutsantonis G.A. J. Organomet. Chem. 295:1985;C40.
60. Pierpont C.G., Eisenberg R. Inorg. Chem. 12:1973;199.
61. Burch R.R., Calabrese J.C. J. Am. Chem. Soc. 108:1986;5359.
62. Pursiainen J., Pakkanen T.A. J. Organomet. Chem. 309:1986;187.
63. Bruce M.I., Humphrey P.A., Snow M.R., Tiekink E.R.T. J. Organomet. Chem. 303:1986;417.
64. Bruce M.I., Humphrey M.G., Snow M.R., Tiekink E.R.T. J. Organomet. Chem. 314:1986;213.
65. Bruce M.I., Catlow A., Humphrey M.G., Koutsantonis G.A., Snow M.R., Tiekink E.R.T. J. Organomet. Chem. 338:1988;59.
66. Sherlock S.J., Cowie M., Singleton E., de V. Steyn M.M. Organometallics. 7:1988;1663.
67. Suravajjala S., Porter L.C. Acta Crystallogr. C (Cr. Str. Comm.). 49:1993;1456.
68. Pearson W.H., Shade J.E., Brown J.E., Bitterwolf T.E. Acta Crystallogr. C (Cr. Str. Comm.). 52:1996;1106.
69. Chang-Ping S., Je-Yu W., He-Fu G., Wen-Qing X., Xiu-Yun L., Jia-Huai W. Jiegou Huaxue (J. Struct. Chem.). 9:1990;301.
70. Lobana T.S., Singh R., Tiekink E.R.T. J. Coord. Chem. 21:1990;225.
71. Massa M.A., Rauchfuss T.B., Wilson S.R. Inorg. Chem. 30:1991;4667.
72. Adams R.D., Li Z., Lii J.-C., Wu W. J. Am. Chem. Soc. 144:1992;4918.
73. N.G. Connelly, P.M. Hopkins, A.G. Orpen, G.M. Rosair, F. Viguri, J. Chem. Soc., Dalton Trans. (1992) 2907.
74. D. Carmona, M.P. Lamata, J. Ferrer, J. Modrego, M. Perales, F.J. Lahoz, R. Atencio, L.A. Oro, J. Chem. Soc., Chem. Comm. (1994) 575.
75. D.D. Pathak, H. Adams, C. White, J. Chem. Soc., Chem. Comm. (1994) 733.
76. J. Lewis, N.A. Page, P.R. Raithby, M. Younus, Private communication, 1995.
77. Schenk W.A., Stur T., Dombrowski E. Inorg. Chem. 31:1992;723.
78. Bruno G., De Munno G., Tresoldi G., Lo Schiavo S., Piraino P. Inorg. Chem. 31:1992;1538.
79. Churchill M.R., Lashewycz R.A. Inorg. Chem. 17:1978;1950.
80. Albano P., Aresta M., Manassero M. Inorg. Chem. 19:1980;1069.
81. D. Touchard, C. Morice, V. Cadiero, P. Haquette, L. Toupet, P.H. Dixneuf, J. Chem. Soc., Chem. Comm. (1994) 859.
82. Polam J.R., Porter L.C. J. Coord. Chem. 29:1993;109.
83. M.C. Hall, B.T. Kilbourn, K.A. Taylor, J. Chem. Soc., A (1970) 2539.
84. McGinnety J.A., Payne N.C., Ibers J.A. J. Am. Chem. Soc. 91:1969;6301.
85. Becalski A.G., Cullen W.R., Fryzuk M.D., James B.R., Kang G.-J., Rettig S.J. Inorg. Chem. 30:1991;5002.
86. K. Kirchner, K. Mauthner, K. Mereiter, R. Schmid, J. Chem. Soc., Chem. Comm. (1993) 892.
87. Tiekink E.R.T., Lobana T.S., Singh R. J. Cryst. Spectro. 21:1991;205.
88. Gargulak J.D., Noirot M.D., Gladfelter W.L. J. Am. Chem. Soc. 113:1991;1054.
89. Ball G.E., Cullen W.R., Fryzuk M.D., James B.R., Rettig S.J. Organometallics. 10:1991;3767.
90. Atherton Z., Faulkner C.W., Ingham S.L., Kakkar A.K., Khan M.S., Lewis J., Long N.J., Raithby P.R. J. Organomet. Chem. 462:1993;265.
91. Gargulak J.D., Gladfelter W.L. Inorg. Chem. 33:1994;253.
92. Adams K.J., McGrath T.D., Welch A.J. Acta Crystallogr. C (Cr. Str. Comm.). 51:1995;401.
93. Faulker C.W., Ingham S.L., Khan M.S., Lewis J., Long N.J., Raithby P.R. J. Organomet. Chem. 482:1994;139.
94. Touchard D., Haquette P., Daridor A., Toupet L., Dixneuf P.H. J. Am. Chem. Soc. 116:1994;11157.
95. Chin B., Lough A.J., Morris R.H., Schweitzer C.T., D'Agostino C. Inorg. Chem. 33:1994;6278.
96. Skoog S.J., Campbell J.P., Gladfelter W.L. Organometallics. 13:1994;4137.
97. Heaton B.T., Jacob C., Smith A.K., Quayle M. Rhodium Express. 1:1993;18.
98. Mauthner K., Mereiter K., Schmid R., Kirchner K. Inorg. Chim. Acta. 236:1995;95.
99. Allen F.H., Kennard O. Chemical Design Automatation News. 8(1):1993;31.
100. Sybyl Version b.1, Tripos, Inc.
101. A.L. Spek, Platon 92, graphic program, University of Utrecht, Netherlands (1992).