Metallocyclic Ferrocenyl Ligands

Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications

Volumn , Issue , 2010, Pages 337-368

  Richards, Christopher J ^a  

^a UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Allylic imidate rearrangement; Diastereoselective metalation; Enantioselective metalation; Palladacycles; Platinacycles; Resolution

Indexed keywords

EID: 77955197469     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527628841.ch12     Document Type: Chapter

References (133)

1. Dupont, J., Pfeffer, M., and Spencer, J. (2001) Eur. J. Inorg. Chem., 1917-1927;
2. Dupont, J., Consorti, C.S., and Spencer, J. (2005) Chem. Rev., 105, 2527-2571;
3. Canty, A.J. (1995) Comprehensive Organometallic Chemistry II, vol. 9, Pergamon, Oxford, New York, pp. 242-248.
4. Djukic, J.-P., Hijazi, A., Flack, H.D., and Bernardinelli, G. (2008) Chem. Soc. Rev., 37, 406-425;
5. Morales-Morales, D., and Jensen, C.M.C (eds) (2007) The Chemistry of Pincer Type Complexes, Elsevier, Amsterdam;
6. Alt, H.G., Licht, E.H., Licht, A.I., and Schneider, K.J. (2006) Coord. Chem. Rev., 250, 2-17;
7. Wu, Y., Huo, S., Gong, J., Cui, X., Ding, L., Ding, K., Du, C., Liu, Y., and Song, M. (2001) J. Organomet. Chem., 637-639, 27-46.
8. Richards, C.J. and Locke, A.J. (1998) Tetrahedron: Asymmetry, 9, 2377-2407;
9. Colacot, T.J. (2003) Chem. Rev., 103, 3101-3118;
10. Arrayás, R.G., Adrio, J., and Carretero, J.C. (2006) Angew. Chem. Int. Ed., 45, 7674-7715.
11. Shintani, R., Lo, M.M.-C., and Fu, G.C. (2000) Org. Lett., 2, 3695-3697;
12. Ganter, C., Brassat, L., Glinsb€ockel, C., and Ganter, B. (1997) Organometallics, 16, 2862-2867.
13. Black, D.S., Deacon, G.B., and Edwards, G.L. (1994) Aust. J. Chem., 47, 217-227.
14. Schl€ogl, K. and Fried, M. (1964) Monatsh. Chem., 95, 558-575;
15. Schl€ogl, K., Fried, M., and Falk, H. (1964) Monatsh. Chem., 95, 576-597.
16. Schl€ogl, K. (1967) Top. Stereochem., 1, 39-91.
17. Cahn, R.S., Ingold, C., and Prelog, V. (1966) Angew. Chem., Int. Ed. Engl., 5, 385-415.
18. Sokolov, V.I., Bulygina, L.A., Babievskii, K.K., and Yamskov, I.A. (2007) Russ. Chem. Bull., Int. Ed., 56, 1464-1466.
19. Cunningham, A.F. (1997) Organometallics, 16, 1114-1122.
20. Cunningham, A.F. (1991) J. Am. Chem. Soc., 113, 4864-4870;
21. Cunningham, A.F. (1994) Organometallics, 13, 2480-2485.
22. Mayor-López, M.J., Weber, J., Mannfors, B., and Cunningham, A.F. (1998) Organometallics, 17, 4983-4991.
23. Ryabov, A.D., Sakodinakaya, I.K., and Yatsimirsky, A.K. (1985) J. Chem. Soc., Dalton Trans., 2629-2638;
24. Ryabov, A.D. (1990) Chem. Rev., 90, 403-424.
25. Davies, D.L., Donald, S.M.A., and Macgregor, S. (2005) J. Am. Chem. Soc., 127, 13754-13755.
26. Moynahan, E.B., Popp, F.D., and Werneke, W.F. (1969) J. Organomet. Chem., 19, 229-232;
27. Gaunt, J.C. and Shaw, B.L. (1975) J. Organomet. Chem., 102, 511-516.
28. Komatsu, T., Nonoyama, M., and Fujita, J. (1981) Bull. Chem. Soc. Jpn., 54, 186-189;
29. Sokolov, V.I., Nechaeva, K.S., and Reutov, O.A. (1983) J. Organomet. Chem., 253, C55-C58.
30. Dunina, V.V., Gorunova, O.N., Livantsov, M.V., Grishin, Y.K., Kuzmima, L.G., Kataeva, N.A., and Churakov, A.V. (2000) Tetrahedron: Asymmetry, 11, 3967-3984.
31. Huo, S.Q., Wu, Y.J., Du, C.X., Zhu, Y., Yuan, H.Z., and Mao, X.A. (1994) J. Organomet. Chem., 483, 139-146.
32. Wu, Y.J., Cui, X.L., Du, C.X., Wang, W.L., Guo, R.Y., and Chen, R.F. (1998) J. Chem. Soc., Dalton Trans., 3727-3730;
33. Cui, X.L.,Wu, Y.J., Du, C.X., Yang, L.R., and Zhu, Y. (1999) Tetrahedron: Asymmetry, 10, 1255-1262.
34. Wu, Y.-J., Ding, L., Wang, W.-L., and Du, C.-X. (1998) Tetrahedron: Asymmetry, 9, 4035-4041.
35. Marquarding, D., Klusacek, H., Gokel, G., Hoffmann, P., and Ugi, I. (1970) J. Am. Chem. Soc., 92, 5389-5393.
36. Gokel, G.W. and Ugi, I.K. (1972) J. Chem. Ed., 49, 294-296;
37. Boaz, N.W. (1989) Tetrahedron Lett., 30, 2061-2064.
38. Sokolov, V.I., Troitskaya, L.L., and Reutov, O.A. (1977) J. Organomet. Chem., 133, C28-C30.
39. López, C., Bosque, R., Solans, X., and Font-Bardia, M. (1996) Tetrahedron: Asymmetry, 7, 2527-2530.
40. Hollis, T.K. and Overman, L.E. (1997) Tetrahedron Lett., 38, 8837-8840.
41. Sokolov, V.I., Troitskaya, L.L., and Bondareva-Don, V.L. (2005) Molecules, 10, 649-652.
42. Sokolov, V.I., Troitskaya, L.L., and Rozhkova, T.I. (1987) Gazz. Chim. Ital., 117, 525-527.
43. Sokolov, V.I., Troitskaya, L.L., Gautheron, B., and Tainturier, G. (1982) J. Organomet. Chem., 235, 369-373.
44. Dunina, V.V., Gorunova, O.N., Livantsov, M.V., Grishin, Y.K., Kuz'mina, L.G., Kataeva, N.A., and Churakov, A.V. (2000) Inorg. Chem. Comm., 3, 354-357.
45. Richards, C.J., Damalidis, T., Hibbs, D.E., and Hursthouse, M.B. (1995) Synlett, 74-76;
46. Sammakia, T., Latham, H.A., and Schaad, D.R. (1995) J. Org. Chem., 60, 10-11;
47. Nishibayashi, Y. and Uemura, S. (1995) Synlett, 79-81.
48. Moyano, A., Rosol, M., Moreno, R.M., López, C., and Maestro, M.A. (2005) Angew. Chem. Int. Ed., 41, 1865-1869.
49. Xia, J.-B. and You, S.-L. (2007) Organometallics, 26, 4869-4871.
50. Peters, R., Xin, Z., Fischer, D.F., and Schweizer, W.B. (2006) Organometallics, 25, 2917-2920.
51. Weiss,M.E., Fischer,D.F., Xin, Z., Jautze, S., Schweizer, W.B., and Peters, R. (2006) Angew. Chem. Int. Ed., 45, 5694-5698.
52. Jautze, S., Seiler, P., and Peters, R. (2007) Angew. Chem. Int. Ed., 46, 1260-1264;
53. Jautze, S., Seiler, P., and Peters, R. (2008) Chem. Eur. J., 14, 1430-1444.
54. Zhao, G., Xue, F., Zhang, Z.-Y., and Mak, T.C.W. (1997) Organometallics, 16, 4023-4026.
55. Zhao, G., Wang, Q.-G., and Mak, T.C.W. (1998) Tetrahedron: Asymmetry, 9, 2253-2257.
56. Benito, M., López, C., Solans, X., and Font-Bardídotlessa, M. (1998) Tetrahedron: Asymmetry, 9, 4219-4238.
57. Zhao, G., Yang, O.-C., and Mak, T.C.W. (1999) Organometallics, 18, 3623-3636.
58. Zhao, G., Wang, Q.-G., and Mak, T.C.W. (1998) Tetrahedron: Asymmetry, 9, 1557-1561;
59. Zhao, G.,Wang, Q.-G., and Mak, T.C.W. (1998) Polyhedron, 17, 1-8.
60. Zhao, G., Wang, Q.-G., and Mak, T.C.W. (1998) Organometallics, 17, 3437-3441.
61. Zhao, G., Wang, Q.-G., and Mak, T.C.W. (1998) J. Chem. Soc., Dalton Trans., 3785-3789.
62. López, C., Caubet, A., Pérez, S., Solans, X., and Font-Bardia, M. (2004) Chem. Comm., 540-541;
63. López, C., Caubet, A., Pérez, S., Solans, X., Font-Bardídotlessa, M., and Molins, E. (2006) Eur. J. Inorg. Chem., 3974-3984.
64. Du, L.-Z., Gong, J.-F., Xu, C., Zhu, Y.,Wu, Y.-J., and Song, M.-P. (2006) Inorg. Chem. Comm., 9, 410-414.
65. Ryabov, A.D., Panyashkina, I.M., Polyakov, V.A., Howard, J.A.K.,Kuz'mina, L.G., Datt, M.S., and Sacht, C. (1998) Organometallics, 17, 3615-3618.
66. Ryabov, A.D., Panyashkina, I.M., Kazankov, G.M., Polyakov, V.A., and Kuz'mina, L.G. (2000) J. Organomet. Chem., 601, 51-56.
67. Wu, Y., Cui, X., Zhou, N., Song, M., Yun, H., Du, C., and Zhu, Y. (2000) Tetrahedron: Asymmetry, 11, 4877-4883.
68. Riant, O., Samuel, O., and Kagan, H.B. (1993) J. Am. Chem. Soc., 115, 5835-5836;
69. Riant, O., Samuel, O., Flessner, T., Taudien, S., and Kagan, H.B. (1997) J. Org. Chem., 62, 6733-6745.
70. Cohen, F. and Overman, L.E. (1998) Tetrahedron: Asymmetry, 9, 3213-3222.
71. Sutcliffe, O.B. and Bryce, M.R. (2003) Tetrahedron: Asymmetry, 14, 2297-2325.
72. Donde, Y. and Overman, L.E. (1999) J. Am. Chem. Soc., 121, 2933-2934;
73. Anderson, C.E., Donde, Y., Douglas, C.J., and Overman, L.E. (2005) J. Org. Chem., 70, 648-657.
74. Locke, A.J., Pickett, T.E., and Richards, C.J. (2001) Synlett, 141-143.
75. Kang, J., Yew, K.H., Kim, T.H., and Choi, D.H. (2002) Tetrahedron Lett., 43, 9509-9512.
76. Wu, Y., Yang, L., Cui, X., Du, C., and Zhu, Y. (2003) Tetrahedron: Asymmetry, 14, 1073-1077.
77. Sokolov, V.I. and Troitskaya, L.L. (1978) Chimia, 32, 122-123;
78. Sokolov, V.I., Troitskaya, L.L., and Reutov, O.A. (1979) J. Organomet. Chem., 182, 537-546.
79. Ryabov, A.D., Firsova, Y.N., Goral, V.N., Ryabov, E.S., Shevelkova, A.N., Troitskaya, L.L., Demeschik, T.V., and Sokolov, V.I. (1999) Chem. Eur. J., 4, 806-813.
80. Ryabov, A.D. and Yatsimirsky, A.K. (1984) Inorg. Chem., 23, 789-790;
81. Ryabov, A.D. (1987) Inorg. Chem., 26, 1252-1260.
82. Dunina, V.V., Razmyslova, E.D., Gorunova, O.N., Livantsov, M.V., and Grishin, Y.K. (2003) Tetrahedron: Asymmetry, 14, 2331-2333;
83. Dunina, V.V., Gorunova, O.N., Kuznetsova, E.D., Turubanova, E.I., Livantsov, M.V., Grishin, Y.K., Kuz'mina, L.G., and Churakov, A.V. (2006) Russ. Chem. Bull., Int. Ed., 55, 2193-2211.
84. Stevens, A.M. and Richards, C.J. (1999) Organometallics, 18, 1346-1348.
85. Prasad, R.S., Anderson, C.E., Richards, C.J., and Overman, L.E. (2005) Organometallics, 24, 77-81.
86. Yeamine, M.R. and Richards, C.J. (2007) Tetrahedron: Asymmetry, 18, 2613-2616.
87. Roca, F.X., Motevalli, M., and Richards, C.J. (2005) J. Am. Chem. Soc., 127, 2388-2389.
88. Wild, S.B. (1997) Coord. Chem. Rev., 166, 291-311.
89. López, C., Bosque, R., Sainz, D., Solans, X., and Font-Bardídotlessa, M. (1997) Organometallics, 16, 3261-3266.
90. Sokolov, V.I., Troitskaya, L.L., and Reutov, O.A. (1980) J. Organomet. Chem., 202, C58-C60.
91. Gruselle, M., Malezieux, B., Sokolov, V.I., and Troitskaya, L.L. (1994) Inorg. Chem. Acta, 222, 51-61;
92. Malézieux, B., Gruselle, M., Troitskaya, L.L., and Sokolov, V.I. (1998) Tetrahedron: Asymmetry, 9, 259-269.
93. Troitskaya, L.L. and Sokolov, V.I. (1985) J. Organomet. Chem., 285, 389-393.
94. Kasahara, A., Izumi, T., and Watabe, H. (1979) Bull. Chem. Soc. Jp., 52, 957-958.
95. Sokolov, V.I., Troitskaya, L.L., and Khrushchova, N.S. (1983) J. Organomet. Chem., 250, 439-446;
96. Sokolov, V.I. (1983) Pure Appl. Chem., 55, 1837-1844.
97. Zhao, G., Wang, Q.-G., and Mak, T.C.W. (1999) J. Organomet. Chem., 574, 311-317.
98. Tsuji, J. (2004) Palladium Reagents and Catalysts: New Perspectives for the 21st Century, Wiley, New York.
99. Wu, Y., Hou, J., Yun, H., Cui, X., and Yuan, R. (2001) J. Organomet. Chem., 637-639, 793-795;
100. Roca, F.X. and Richards, C.J. (2003) Chem. Comm., 3002-3003;
101. Gong, J., Liu, G., Du, C., Zhu, Y., and Wu, Y. (2005) J. Organomet. Chem., 690, 3963-3969;
102. Xu, C., Gong, J.-F., Yue, S.-F., Zhu, Y., and Wu, Y.-J. (2006) Dalton Trans., 4730-4739;
103. Xu, C., Gong, J.-F., and Wu, Y.-J. (2007) Tetrahedron Lett., 48, 1619-1623;
104. Li, J., Cui, M., Yu, A., and Wu, Y. (2007) J. Organomet. Chem., 692, 3732-3742;
105. Mu, B., Li, T., Xu,W., Zeng, G., Liu, P., and Wu, Y. (2007) Tetrahedron, 63, 11475-11488;
106. Cui, M., Li, J., Yu, A., Zhang, J., and Wu, Y. (2008) J. Mol. Cat. A, 290, 67-71.
107. Phan, N.T.S., Sluys, M.V.D., and Jones, C.W. (2006) Adv. Synth. Catal., 348, 609-679.
108. Overman, L.E. (1974) J. Am. Chem. Soc., 96, 597-599;
109. Overman, L.E. (1976) J. Am. Chem. Soc., 98, 2901-2910;
110. Overman, L.E. (1980) Acc. Chem. Res., 13, 218-224.
111. Ikariya, T., Ishikawa, Y., Hirai, K., and Yoshikawa, S. (1982) Chem. Lett., 1815-1818;
112. Schenck, T.G. and Bosnich, B. (1985) J. Am. Chem. Soc., 107, 2058-2066;
113. Metz, P., Mues, C., and Schoop, A. (1992) Tetrahedron, 48, 1071-1080;
114. Mehmandoust, M., Petit, Y., and Larchevêque, M. (1992) Tetrahedron Lett., 33, 4313-4316;
115. Gonda, J., Helland, A.-C., Ernst, B., and Belluš, D. (1993) Synthesis, 729-734;
116. Overman, L.E. and Zipp, G.G. (1997) J. Org. Chem., 62, 2288-2291.
117. Calter, M., Hollis, T.K., Overman, L.E., Ziller, J., and Zipp, G.G. (1997) J. Org. Chem., 62, 1449-1456;
118. Uozumi, Y., Kato, K., and Hayashi, T. (1998) Tetrahedron: Asymmetry, 9, 1065-1072.
119. Fischer, D.F., Xin, Z., and Peters, R. (2007) Angew. Chem. Int. Ed., 46, 7704-7707.
120. Overman, L.E., Owen, C.E., Pavan, M.M., and Richards, C.J. (2003) Org. Lett., 5, 1809-1812.
121. Anderson, C.E. and Overman, L.E. (2003) J. Am. Chem. Soc., 125, 12412-12413.
122. Anderson, C.E., Overman, L.E., and Watson, M.P. (2005) Org. Synth., 82, 134-137.
123. Kirsch, S.F., Overman, L.E., and Watson, M.P. (2004) J. Org. Chem., 69, 8101-8104.
124. Nomura, H. and Richards, C.J. (2007) Chem. Eur. J., 13, 10216-10224.
125. Lee, E.E. and Batey, R.A. (2005) J. Am. Chem. Soc., 127, 14887-14893.
126. Kang, J., Kim, T.H., Yew, K.H., and Lee, W.K. (2003) Tetrahedron: Asymmetry, 14, 415-418.
127. Overman, L.E. (1984) Angew. Chem., Int. Ed. Engl., 23, 579-586.
128. Watson, M.P., Overman, L.E., and Bergman, R.G. (2007) J. Am. Chem. Soc., 129, 5031-5044.
129. Kirsch, S.F. and Overman, L.E. (2005) J. Am. Chem. Soc., 127, 2866-2867.
130. Binder, J.T. and Kirsch, S.F. (2007) Chem. Comm., 4164-4166.
131. Kirsch, S.F., Overman, L.E., and White, N.S. (2007) Org. Lett., 9, 911-913.
132. Overman, L.E. and Remarchuk, T.P. (2002) J. Am. Chem. Soc., 124, 12-13.
133. Kirsch, S.F. and Overman, L.E. (2005) J. Org. Chem., 70, 2859-2861.