Bidentate 1,2-Ferrocenyl Diphosphine Ligands

Chiral Ferrocenes in Asymmetric Catalysis: Synthesis and Applications

Volumn , Issue , 2010, Pages 73-95

  Blaser, Hans Ulrich ^a   Lotz, Matthias ^a  

^a SOLVIAS AG   (Switzerland)

Author keywords

Bidentate 1,2 ferrocenyl ligand; Bophoz ligand; Industrial applications of ferrocenyl ligands; Josiphos ligand; Ru catalyzed hydrogenation; Taniaphos ligand; TRAP ligand; Walphos ligand

Indexed keywords

EID: 84878985345     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527628841.ch4     Document Type: Chapter

References (135)

1. Hayashi, T. (1995) Ferrocenes (eds A. Togni and T. Hayashi) VCH, Weinheim, p. 105.
2. Colacot, T.J. (2003) Chem. Rev., 103, 3101;
3. Dai, L.-X., Tu, T., You, S.-L., Deng, W.-P., and Hou, X.-L. (2003) Acc. Chem. Res., 36, 659;
4. Barbaro, P., Bianchini, C., Giambastiani, G., and Parisel, S.L. (2004) Coord. Chem. Rev., 248, 2131;
5. Atkinson, R.C.J., Gibson, V.C., and Long, N.J. (2004) Chem. Soc. Rev., 33, 313;
6. Arrayás, R.G., Adrio, J., and Carretero, J.C. (2006) Angew. Chem. Int. Ed., 45, 7674.
7. Chen,W. and Blaser, H.U. (2008) Trivalent Phosphorus Compounds in Asymmetric Catalysis: Synthesis and Applications (ed. A. B€orner) Wiley-VCH Verlag GmbH, Weinheim, p. 345 and 359.
8. Argouarch, G., Samuel, O., Riant, O., Daran, J.-C., and Kagan, H.B. (2000) Eur. J. Org. Chem., 2893.
9. Togni, A., Breutel, C., Schnyder, A., Spindler, F., Landert, H., and Tijani, A. (1994) J. Am. Chem. Soc., 116, 4062.
10. Blaser, H.U., Buser, H.P., Coers, K., Hanreich, R., Jalett, H.P., Jelsch, E., Pugin, B., Schneider, H.D., Spindler, F., and Wegmann, A. (1999) Chimia, 53, 275.
11. Blaser, H.U., Brieden, W., Pugin, B., Spindler, F., Studer, M., and Togni, A. (2002) Top. Catal., 19, 3;
12. Thommen, M. and Blaser, H.U.(July/August (2002)) PharmaChem, 33 and http://www.solvias.com/english/products-and-services/chemicals/ligands/chiral-ligand-kit.html.
13. Togni, A., Breutel, C., Soares, M.C., Zanetti, N., Gerfin, T., Gramlich, V., Spindler, F., and Rihs, G. (1994) Inorg. Chim. Acta, 222, 213;
14. Gambs, C., Consiglio, G., and Togni, A. (2001) Helv. Chim. Acta, 84, 3105.
15. Blaser, H.U., Spindler, F., and Thommen, M. (2007) Handbook of Homogeneous Hydrogenation (eds J.G. de Vries and C.J. Elsevier), Wiley-VCH Verlag GmbH, Weinheim, p. 1279.
16. Blaser, H.U. (2002) Adv. Synth. Catal., 344, 17.
17. Rouhi, M. (2004) C&EN, 82 (37), 28;
18. Hsiao, Y., Rivera, N.R., Rosner, T., Krska, S.W., Njolito, E., Wang, F., Sun, Y., Armstrong, J.D., Grabowski, E.J.J., Tillyer, R.D., Spindler, F., and Malan, C. (2004) J. Am. Chem. Soc., 126, 9918;
19. Kubryk, M. and Hansen, K.B. (2006) Tetrahedron: Asymmetry, 17, 205;
20. Clausen, A.M., Dziadul, B., Cappuccio, K.L., Kaba, M., Starbuck, C., Hsiao, Y., and Dowling, T.M. (2006) Org. Proc. Res. Devel., 10, 723.
21. Ikemoto, T., Nagata, T., Yamano, M., Ito, T., Mizuno, Y., and Tomimatsu, K. (2004) Tetrahedron Lett., 45, 7757.
22. Shultz, C.S., Dreher, S.D., Ikemoto, N., Williams, J.M., Grabowski, E.J.J., Krska, S.W., Sun, Y., Dormer, P.G., and DiMichele, L. (2005) Org. Lett., 7, 3405.
23. Allwein, S.P., McWilliams, J.C., Secord, E.A., Mowrey, D.R., Nelson, T.D., and Kress, M.H. (2006) Tetrahedron Lett., 47, 6409.
24. Baratta, W., Ballico, M., Del Zotto, A., Siega, K.,Magnolia, S., and Rigo, P. (2008) Chem. Eur. J., 14, 2557;
25. Baratta, W., Cheluccci, G.,Herdtweck, E.,Magnolia, S., Siega, K., and Rigo, P. (2007) Angew. Chem. Int. Ed., 46, 7651.
26. Czekelius, C. and Carreira, E.M. (2003) Angew. Chem. Int. Ed., 42, 4793;
27. Czekelius, C. and Carreira, E.M. (2004) Org. Lett., 6, 4575.
28. Lipshutz, B.H. and Servesko, J.M. (2003) Angew. Chem. Int. Ed., 42, 4789;
29. Lipshutz, B.H., Servesko, J.M., and Taft, B.R. (2004) J. Am. Chem. Soc., 126, 8352;
30. Lipshutz, B.H., Tanaka, N., Taft, B.R., and Lee, C.-T. (2006) Org. Lett., 8, 1963;
31. Lipshutz, B.H., Lee, C.-T., and Serversko, J.M. (2007) Org. Lett., 9, 4713.
32. Lee, D., Kim, D., and Yun, J. (2006) Angew. Chem. Int. Ed., 45, 2785.
33. Andresen, B.M., Caron, S., Couturier, M., DeVries, K.M., Do, N.M., Dupont, K., Gosh, A., Girardin, M., Hawkins, J.M., Makowski, T.M., Riou, M., Sieser, J.E., Tucker, J.L., Vanderplas, B.C., and Watson, T.J.N. (2006) Chimia, 60, 554.
34. Makino, K., Fijii, T., and Hamada, Y. (2006) Tetrahedron: Asymmetry, 17, 481.
35. Lopez, F.,Harutyunyan, S.R.,Meetsma, A., Minnaard, A.J., and Feringa, B.L. (2005) Angew. Chem. Int. Ed., 44, 2752;
36. Des Mazery, R., Pullez, M., Lopez, F., Harutyunyan, S.R., Minnaard, A.J., and Feringa, B.L. (2005) J. Am. Chem. Soc., 127, 9966;
37. Howell, G.P., Fletcher, S.P., Geurts, K., ter Horst, B., and Feringa, B.L. (2006) J. Am. Chem. Soc., 128, 14977;
38. Feringa, B.L., Badorrey, R., Pena, D., Harutyunyan, S.R., and Minnaard, A.J. (2004) Proc. N. Y. Acad. Sci., 101, 5834;
39. Den Hartog, T., Harutyunyan, S.R., Font, D., Minnaard, A.J., and Feringa, B.L. (2008) Angew. Chem. Int. Ed., 47, 398.
40. Pucheault, M., Darses, S., and Genêt, J.-P. (2002) Eur. J. Org. Chem., 3552.
41. Lautens, M., Fagnou, K., and Hiebert, S. (2003) Acc. Chem. Res., 36, 48;
42. Lautens, M. and Fagnou, K. (2004) Proc. N. Y. Acad. Sci., 101, 5455;
43. SolviasAGunpublished results.
44. Bercot, E.A. and Rovis, T. (2004) J. Am. Chem. Soc., 126, 10248.
45. Leitner, A., Larsen, J., Steffen, C., and Hartwig, J.F. (2004) J. Org. Chem., 69, 7552.
46. Lormann, M.E.P., Nieger, M., and Br€ase, S. (2006) J. Organomet. Chem., 691, 2159.
47. Goddard, C., Ruiz, A., and Claver, C. (2006) Helv. Chim. Acta, 89, 161.
48. Xu, G. and Han, L.-B. (2006) Org. Lett., 8, 2099.
49. Yamamoto, Y., Takada, S., and Miyaura, N. (2006) Chem. Lett., 35, 1368.
50. Shen, Q. and Hartwig, J.F. (2006) J. Am. Chem. Soc., 128, 10028;
51. Fernandez-Rodriguez, M.A., Shen, Q., and Hartwig, J.F. (2006) J. Am. Chem. Soc., 128, 2180;
52. Limmert, M.E., Roy, A.H., and Hartwig, J.F. (2005) J. Org. Chem., 70, 9364.
53. Cai, C., Rivera, N.R., Balsells, J., Sidler, R.R., McWilliam, J.C., Shultz, C.S., and Sun, Y. (2006) Org. Lett., 8, 5161.
54. Feng,X., Pugin, B., K€usters, E., Sedelmeier, G., and Blaser, H.U. (2007) Adv. Synth. Catal., 349, 1803.
55. Pugin, B., Landert, H., Spindler, F., and Blaser, H.-U. (2002) Adv. Synth.Catal., 344, 974.
56. K€ollner, C., Pugin, B., and Togni, A. (1998) J. Am. Chem. Soc., 120, 10274.
57. Hems, W.P., McMorn, P., Riddel, S., Watson, S.,Hancock, F.E., and Hutchings, G.J. (2005) Org. Biomol. Chem., 3, 1547.
58. Stephenson, P., Kondor, B., Licence, P., Scovell, K., Ross, S.K., and Poliakoff, M. (2006) Adv. Synth. Catal., 348, 1605.
59. Argouarch, G., Samuel, O., and Kagan, H.B. (2000) Eur. J. Org. Chem., 2885.
60. Yasuike, S., Kofink, C.C., Kloetzing, R.J., Gommermann, N., Tappe, K.,Gavryushin, A., and Knochel, P. (2005) Tetrahedron: Asymmetry, 16, 3385.
61. SolviasAGunpublished screening results.
62. Sturm, T.,Weissensteiner,W., Spindler, F., Mereiter, K., Lopez-Agenjo, A.M., Manzano, B.R., and Jalon, F.A. (2002) Organometallics, 21, 1766.
63. Cayuela, E.M., Xiao, L., Sturm, T., Manzano, B.R., Jalon, F.A., and Weissensteiner, W. (2000) Tetrahedron: Asymmetry, 11, 861;
64. Mernyi, A., Kratky, C., Weissensteiner, W., and Widhalm, M. (1996) J. Organomet. Chem., 508, 209.
65. Sturm, T., Abad, B., Weissensteiner, W., Mereiter, K., Manzano, B.R., and Jalon, F.A. (2006) J. Mol. Catal. A: General, 255, 209.
66. Boaz, N.W., Debenham, D.D., Mackenzie, E.B., and Large, S.E. (2002) Org. Lett., 4, 2421;
67. Boaz, N.W., Mackenzie, E.B., Debenham, S.D., Large, S.E., and Ponasik, J.A. Jr (2005) J. Org. Chem., 70, 1872;
68. Boaz, N.W., Ponasik, J.A., and Large, S.E. (2005) Tetrahedron: Asymmetry, 16, 2063
69. Boaz, N.W., Debenham, S.D., Large, S.E., and Moore, M.K. (2003) Tetrahedron: Asymmetry, 14, 3575;
70. Boaz, N.W., Large, S.E., Posniak, J.A., Moore, M.K., Barnett, T., and Nottingham, W.D. (2005) Org. Proc. Res. Dev., 9, 472;
71. Boaz, N.W., Ponasik, J.A., and Large, S.E. (2006) Tetrahedron Lett., 47, 4033.
72. http://www.jmcatalysts.com/pct/producttype.asp?producttypeid1/4265.
73. Jia, X., Li, X., Lam, W.S., Kok, S.H.L., Xu, L., Lu, G., Yeung, C., and Chan, A.S.C. (2004) Tetrahedron: Asymmetry, 15, 2273.
74. Li, X., Jia, X., Xu, L., Kok, S.H.L., Yip, C.W., and Chan, A.S.C. (2005) Adv. Synth. Catal., 347, 1904.
75. Lauzon, C. and Charette, A.B. (2006) Org. Lett., 8, 2734.
76. Chen, W., Mbafor, W., Roberts, S.M., and Whittall, J. (2006) J. Am. Chem. Soc., 128, 3922;
77. Chen,W., McCormack, P.J., Mohammed, K., Mbafor, W., Roberts, S.M., and Whittall, J. (2007) Angew. Chem Int. Ed., 46, 4141.
78. Hu, X. and Zheng, Z. (2005) Org. Lett., 7, 419;
79. Hu, X. and Zheng, Z. (2004) Org. Lett., 6, 3585.
80. Xiao, L., Mereiter, K., Spindler, F., and Weissensteiner, W. (2001) Tetrahedron: Asymmetry, 12, 1105.
81. Lotz, M., Kramer, G., and Knochel, P. (2002) Chem. Comm., 2546.
82. Nettekoven, U., Widhalm, M., Kamer, P.C.J., van Leeuwen, P.W.N.M., Mereiter, K., Lutz, M., and Spek, A.L. (2000) Organometallics, 19, 2299;
83. Nettekoven, U., Widhalm, M., Kalchhauser, H., Kamer, P.C.J., van Leeuwen, P.W.N.M., Lutz, M., and Spek, A.L. (2001) J. Org. Chem., 66, 759.
84. Ireland, T., Grossheimann, G., Wieser-Jeunesse, C., and Knochel, P. (1999) Angew. Chem. Int. Ed., 38, 3212;
85. Ireland, T., Tappe, K., Grossheimann, G., and Knochel, P. (2002) Chem. Eur. J., 8, 843;
86. Lotz, M., Polborn, K., and Knochel, P. (2002) Angew. Chem. Int. Ed., 41, 4708;
87. Tappe, K. and Knochel, P. (2004) Tetrahedron: Asymmetry 15, 91.
88. Fukuzawa, S., Yamamoto, M., Hosaka, M., and Kikuchi, S., (2007) Eur. J. Org. Chem., 5540.
89. Spindler, F., Malan, C., Lotz, M., Kesselgruber, M., Pittelkow, U., Rivas-Nass, A., Briel, O., and Blaser, H.U. (2004) Tetrahedron: Asymmetry, 15, 2299.
90. Lautens, M., Fagnou, K., and Zunic, V. (2002) Org. Lett., 4, 3465.
91. Chuzel, O.,Deschamp, J.,Chausteur, C., and Riant, O. (2006) Org. Lett., 8, 5943;
92. Deschamp, J., Chuzel, O., Hannedouche, J., and Riant, O. (2006) Angew. Chem. Int. Ed., 45, 1292.
93. Zhao, D., Oisaki, K., Kanai, M., and Shibasaki, M. (2006) J. Am. Chem. Soc., 128, 14440.
94. Oisaki, K., Zhao, D., Kanai, M., and Shibasaki, M. (2006) J. Am. Chem. Soc., 128, 7164.
95. Llamas, T., Gomez Arrayas, R., and Carretero, J.C. (2006) Org. Lett., 8, 1795.
96. Lopez, F., van Zijl, A.W., Minnaard, A.J., and Feringa, B.L. (2006) Chem. Comm., 409;
97. Geurts, K., Fletcher, S.P., and Feringa, B.L. (2006) J. Am. Chem. Soc., 128, 15572;
98. Chen, W., Roberts, S.M., Whittall, J., and Steiner, A. (2006) Chem. Comm., 2916.
99. Longmire, J.M., Wang, B., and Zhang, X. (2000) Tetrahedron Lett., 41, 5435;
100. Longmire, J.M., Wang, B., and Zhang, X. (2002) J. Am. Chem. Soc., 124, 13400.
101. You, S.-L., Hou, X.-L., Dai, L.-X., Cao, B.-X., and Sun, J. (2000) Chem. Comm., 1933;
102. You, S.-L., Hou, X.-L., and Zhu, X.-Z. (2001) Org. Lett., 3, 149;
103. You, S.-L., Zhu, X.-Z., Luo, Y.M., Hou, X.L., and Dai, L.-X. (2001) J. Organomet. Chem., 637-639, 762.
104. Sturm, T., Xiao, L., andWeissensteiner,W. (2001) Chimia, 55, 688.
105. Morgan, J.B. and Morken, J.P. (2004) J. Am. Chem. Soc., 126, 15338.
106. Moran, W.J. and Morken, J.P. (2006) Org. Lett., 6, 2413.
107. Moberg, V., Haukka, M., Koshevoy, I.O., Ortiz, R., and Nordlander, E. (2007) Organometallics, 26, 4090.
108. Sturm, T., Weissensteiner, W., and Spindler, F. (2003) Adv. Synth. Catal., 345, 160.
109. Houpis, I.N., Patterson, L.E., Alt, C.A., Rizzo, J.R., Zhang, T.Y., and Haurez, M. (2005) Org. Lett., 7, 1947.
110. Tanaka, K., Hagiwara, Y., and Noguchi, K. (2005) Angew. Chem. Int. Ed., 44, 7260.
111. Kong, J.-R., Ngai, M.-Y., and Krische, M.J. (2006) J. Am. Chem. Soc., 128, 718;
112. Komanduri, V. and Krische, M.J. (2006) J. Am. Chem. Soc., 128, 16448.
113. Jana, C.K. and Studer, A. (2007) Angew. Chem. Int. Ed., 46, 6542-6544.
114. Sawamura, M., Hamashima, H., and Ito, Y. (1991) Tetrahedron: Asymmetry, 2, 593;
115. Sawamura, M., Hamashima, H., Sugawara, M., Kuwano, R., and Ito, Y. (1995) Organometallics, 14, 4549;
116. Kuwano, R., Sawamura, M., Okuda, S., Asai, T., Ito, Y., Redon, M., and Krief, A. (1997) Bull. Chem. Soc. Jpn., 70, 2807.
117. Kuwano, R., Okuda, S., and Ito, Y. (1998) Tetrahedron: Asymmetry, 9, 2773;
118. Kuwano, R., Okuda, S., and Ito, Y. (1998) J. Org. Chem., 63, 3499;
119. Kuwano, R., Sawamura, M., and Ito, Y. (2000) Bull. Chem. Soc. Jpn., 73, 2571;
120. Kuwano, R. and Ito, Y. (1999) J. Org. Chem., 64, 1232;
121. Kuwano, R., Sato, K., Kurokawa, T., Karube, D., and Ito, Y. (2000) J. Am. Chem. Soc., 122, 7614;
122. Kuwano, R., Kashiwabara, M., Sato, K., Ito, T., Kaneda, K., and Ito, Y. (2006) Tetrahedron: Asymmetry, 17, 521;
123. Kuwano, R., Kaneda, K., Ito, T., Sato, K., Kurokawa, T., and Ito, Y. (2004) Org. Lett., 6, 2213;
124. Kuwano, R. and Kashiwabara, M. (2006) Org. Lett., 8, 2653.
125. Sawamura, M., Kuwano, R., and Ito, Y. (1994) Angew. Chem. Int. Ed., 33, 111;
126. Kuwano, R., Sawamura, M., Shirai, J., Takahashi, M., and Ito, Y., (2000) Bull. Chem. Soc. Jpn., 73, 485.
127. Sawamura, M., Hamashima, H., and Ito, Y. (1992) J. Am. Chem. Soc., 114, 8295;
128. Sawamura, M., Hamashima, H., and Ito, Y. (1994) Tetrahedron, 50, 439;
129. Sawamura, M., Hamashima, H., Shinoto, H., and Ito, Y. (1995) Tetrahedron Lett., 36, 6479;
130. Sawamura, M., Hamashima, H., and Ito, Y. (2000) Bull. Chem. Soc. Jpn., 73, 2559.
131. Kuwano, R., Miyazaki, H., and Ito, Y. (1998) Chem. Comm., 71;
132. Kuwano, R., Miyazaki, H., and Ito, Y. (2000) J. Organomet. Chem., 603, 18.
133. Sawamura, M., Sudoh, M., and Ito, Y. (1996) J. Am. Chem. Soc., 118, 3309.
134. Goeke, A., Sawamura, M., Kuwano, R., and Ito, Y. (1996) Angew. Chem. Int. Ed, 35, 662.
135. Kuwano, R., Uemura, T., Saitoh, M., and Ito, Y. (2004) Tetrahedron: Asymmetry, 15, 2263.