Enantioselective Carbonylation Reactions

Modern Carbonylation Methods

Volumn , Issue , 2008, Pages 65-92

  Claver, Carmen ^a   Godard, Cyril ^a   Ruiz, Aurora ^a   Pàmies, Oscar ^a   Diéguez, Montserrat ^a  

^a UNIVERSITAT ROVIRA I VIRGILI   (Spain)

Author keywords

Alkoxycarbonylation reactions; Enantioselective carbonylation reactions; Modern carbonylation methods; Pd catalyzed asymmetric hydroxy reactions; Rhodium catalyzed asymmetric hydroformylation

Indexed keywords

EID: 84891008542     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527621545.ch3     Document Type: Chapter

References (128)

1. van Leeuwen, P.W.N.M. and Claver, C. (eds) (2000) Rhodium Catalyzed Hydroformylation, Kluwer Academic Press, Dordrecht.
2. Claver, C., Dieguez, M., Pamies, O. and Castillon, S., (2006) Topics in Organometallic Chemistry, Catalytic Carbonylation Reactions, Asymmetric Hydroformylation, vol. 18, Springer GmbH, Berlin, p. 35.
3. van Leeuwen, P.W.N.M., Casey, C.P. and Whiteker, G.T. (2000) Rhodium Catalyzed Hydroformylation (eds P.W.N.M. van Leeuwen and C. Claver), Kluwer Academic Press, Dordrecht, Chapter 4, p. 63.
4. Breit, B. and Seiche, W. (2001) Synthesis, 1.
5. Castillón, S. and Férnandez, E. (2000) Rhodium Catalyzed Hydroformylation (eds P.W.N.M. van Leeuwen and C. Claver), Kluwer Academic Press, Dordrecht, Chapter 6, p. 145.
6. Botteghi, C., Marchetti, M. and Paganelli, S. (1998) Transition metals for organic synthesis, in Building Blocks and Fine Chemicals, vol. 1 (eds M. Beller and C. Bolm), Wiley-VCH Verlag GmbH, Weinheim, Germany, p. 25.
7. Nozaki, K. and Ojima, I. (2000) Catalytic Asymmetric Synthesis, 2nd edn (ed. I. Ojima), Wiley-VCH Verlag GmbH, New York, Chapter 7.
8. Chapuis, C. and Jacoby, D. (2001) Applied Catalysis, 229, 93.
9. Agbossou, F.F., Carpentier, J.F. and Mortreux, A. (1995) Chemical Reviews, 95, 2485.
10. Gladiali, S., Bayón, J.C. and Claver, C. (1995) Tetrahedron: Asymmetry, 7, 1453.
11. Beller, M., Cornils, B., Frohming, C.D. and Kohlpaintner, C.W. (1995) Journal of Molecular Catalysis, 104, 17.
12. For a complete discussion including the detailed aspects of the different steps in this catalytic cycle see van Leeuwen, P.W.N.M. (2004) Homogeneous Catalysis: Understanding the Art, Kluwer Academic Publishers, Dordrecht, Chapter 8, p. 141.
13. Wink, J.D., Kwok, T.J. and Yee, A. (1990) Inorganic Chemistry, 29, 5007.
14. Sakai, N., Nozaki, K., Mashima, K. and Takaya, H. (1992) Tetrahedron: Asymmetry, 3, 581.
15. Babin, J.E. and Whiteker, G.T. (1993) WO 93/03839 (to Union Carbide Chemicals & Plastics Technology Corporation), Chemical Abstracts, 1993, 119, P159872h.
16. Buisman, G.J.H., van deer Veen, L.A., Klootwijk, A., de Lange, W.G.J., Kamer, P.C.J., van Leeuwen, P.W.N.M. and Vogt, D. (1997) Organometallics, 16, 2929.
17. Buisman, G.J.H., Vos, E.J., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1995) Journal of the Chemical Society, Dalton Transactions, 409.
18. Cserépi-Szûcs, S., Tóth, I., Párkányi, L. and Bakos, J. (1998) Tetrahedron: Asymmetry, 9, 3135.
19. HRh(CO)2(diphosphite) species are known to be in the resting state in the hydroformylation reaction. See for instance Ref. [1].
20. Buisman, G.J.H., vanderVeen, L.A., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1997) Organometallics, 16, 5681.
21. Diéguez, M., Pàmies, O., Ruiz, A., Castillón, S. and Claver, C. (2000) Journal of the Chemical Society, Chemical Communications, 1607.
22. Diéguez, M., Pàmies, O., Ruiz, A., Castillón, S. and Claver, C. (2001) Chemistry-A European Journal, 7, 3086.
23. Diéguez, M., Pàmies, O., Ruiz, A. and Claver, C. (2002) New Journal of Chemistry, 26, 827.
24. Pàmies, O., Net, G., Ruiz, A. and Claver, C. (2000) Tetrahedron: Asymmetry, 11, 1097.
25. Diéguez, M., Ruiz, A. and Claver, C. (2003) Journal of the Chemical Society, Dalton Transactions, 2957.
26. Buisman, G.J.H., Martin, M.E., Vos, E.J., Klootwijk, A., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (1995) Tetrahedron: Asymmetry, 8, 719.
27. Diéguez, M., Pàmies, O. and Claver, C. (2005) Journal of the Chemical Society, Chemical Communications, 1221.
28. Cobley, C.J., Gardner, K., Klosin, J., Praquin, C., Hill, C., Whiteker, G.T., Zanotti-Gerosa, A., Petersen, J.L. and Abboid, K.A. (2004) The Journal of Organic Chemistry, 69, 4031.
29. Cserépi-Szûcs, S., Huttner, G., Zsolnai, L. and Bakos, J. (1999) Journal of Organometallic Chemistry, 586, 70.
30. Cserépi-Szûcs, S., Huttner, G., Zsolnai, L., Szölösy, A., Hegebüs, C. and Bakos, J. (1999) Inorganica Chimica Acta, 296, 222.
31. Vegehetto, V., Scrivanti, A. and Matteoli, U. (2001) Catalysis Communications, 2, 139.
32. Jiang, Y., Xue, S., Li, Z., Deng, J., Mi, A. and Chan, A.S.C. (1998) Tetrahedron: Asymmetry, 9, 3185.
33. Jiang, Y., Xue, S., Yu, K., Li, Z., Deng, J., Mi, A. and Chan, A.S.C. (1999) Journal of Organometallic Chemistry, 586, 159.
34. Kadyrov, R., Heller, D. and Selke, R. (1999) Tetrahedron: Asymmetry, 9, 329.
35. Freixa, Z. and Bayón, J.C. (2001) Journal of the Chemical Society, Dalton Transactions, 2067.
36. Sakai, N., Mano, S., Nozaki, K. and Takaya, H. (1993) Journal of the American Chemical Society, 115, 7033.
37. Nozaki, K., Sakai, N., Nanno, T., Higashijima, T., Mano, S., Horiuchi, T. and Takaya, H. (1997) Journal of the American Chemical Society, 119, 4413.
38. Nozaki, K., Matsuo, T., Shibahara, F. and Hiyama, T. (2001) Advanced Synthesis & Catalysis, 343, 61.
39. Nozaki, K., Matsuo, T., Shibayara, F. and Hiyama, T. (2003) Organometallics, 22, 594.
40. Nozaki, K., Itoi, Y., Shibayara, F., Shirakawa, E., Ohta, T., Takaya, H. and Hiyama, T. (1998) Journal of the American Chemical Society, 120, 4051.
41. Nozaki, K., Shibahara, F., Itoi, Y., Shirakawa, E., Ohta, T., Takaya, H. and Hiyama, T. (1999) Bulletin of the Chemical Society of Japan, 72, 1911.
42. Franciò, G. and Leitner, W. (1999) Journal of the Chemical Society, Chemical Communications, 1663.
43. Franciò, G., Wittmann, K. and Leitner, W. (2001) Journal of Organometallic Chemistry, 621, 130.
44. Lambers-Verstappen, M.M.H. and de Vries, J.G. (2003) Advanced Synthesis & Catalysis, 345, 478.
45. Nozaki, K., Li, W., Horiuchi, T. and Takaya, H. (1997) Tetrahedron Letters, 38, 4611.
46. Horiuchi, T., Ohta, T., Nozaki, K. and Takaya, H. (1996) Journal of the Chemical Society, Chemical Communications, 155.
47. Horiuchi, T., Ohta, T., Shirakawa, E., Nozaki, K. and Takaya, H. (1997) Tetrahedron: Asymmetry, 53, 7795.
48. Horiuchi, T., Ohta, T., Shirakawa, E., Nozaki, K. and Takaya, H. (1997) The Journal of Organic Chemistry, 62, 4285.
49. Nanno, T., Sakai, N., Nozaki, K. and Takaya, H. (1995) Tetrahedron: Asymmetry, 6, 2583.
50. Nozaki, K., Li, W., Horiuchi, T. and Takaya, H. (1996) The Journal of Organic Chemistry, 61, 7658.
51. Deeremberg, S., Kamer, P.C.J. and van Leeuwen, P.W.N.M. (2000) Organometallics, 19, 2065.
52. Pàmies, O., Net, G., Ruiz, A. and Claver, C. (2001) Tetrahedron: Asymmetry, 12, 3441.
53. Arena, C.G., Faraone, F., Graiff, C. and Tiripicchio, A. (2002) European Journal of Inorganic Chemistry, 711.
54. Rampf, F.A. and Herrmann, W.A. (2000) Journal of Organometallic Chemistry, 601, 138.
55. Breeden, S., Cole-Hamilton, D.J., Foster, D.F., Schwarz, G.J. and Wills, M. (2000) Angewandte Chemie-International Edition, 39, 4106.
56. Clarkson, G.J., Ansel, J.R., Cole-Hamilton, D.J., Pogorzelec, P.J., Whittell, J. and Mills, M. (2004) Tetrahedron: Asymmetry, 15, 1787.
57. Yan, Y. and Zhang, X. (2006) Journal of the American Chemical Society, 128, 7198.
58. Lot, O., Suisse, I., Mortreux, A. and Agbossou, F. (2000) Journal of Molecular Catalysis A: Chemical, 164, 125.
59. Diéguez, M., Ruiz, A. and Claver, C. (2001) Tetrahedron: Asymmetry, 12, 2827.
60. Naili, S., Suisse, I., Mortreux, A., Agbossou-Niedercorn, F. and Nowogrocki, G. (2001) Journal of Organometallic Chemistry, 628, 114.
61. Cessarotti, E., Araneo, S., Rimoldi, I. and Tassi, S. (2003) Journal of Molecular Catalysis A: Chemical, 204-205, 211.
62. Ewalds, R., Eggeling, E.B., Hewat, A.C., Kamer, P.C.J., van Leeuwen, P.W.N.M. and Voght, D. (2000) Chemistry-A European Journal, 6, 1496.
63. Pàmies, O., Diéguez, M., Net, G., Ruiz, A. and Claver, C. (2000) Organometallics, 19, 1488.
64. Saluzzo, C., Breuzard, J., Pellet-Rostaing, S., Vallet, M., Guyader, F.L. and Lemaire, M. (2002) Journal of Organometallic Chemistry, 643-644, 98.
65. Franció, G., Drommi, D., Graiff, C., Faraone, F. and Tiripicchio, A. (2002) Inorganica Chimica Acta, 338, 59.
66. Beller, M., Seayad, J., Tillack, A. and Jiao, H. (2004) Angewandte Chemie-International Edition, 43, 3368.
67. Knifton, J. (1976) The Journal of Organic Chemistry, 41, 793.
68. Cavinato, G. and Toniolo, L. (1990) Journal of Organometallic Chemistry, 398, 187.
69. Milstein, D. (1988) Accounts of Chemical Research, 21, 428.
70. Kanawa, M., Nakamura, S., Watanabe, E. and Urata, H. (1997) Journal of Organometallic Chemistry, 542, 185.
71. del Ro, I., Claver, C. and van Leeuwen, P.W.N.M. (2001) European Journal of Inorganic Chemistry, 2719, and references therein.
72. Ali, B.E. and Alper, H. (1993) Journal of Molecular Catalysis, 80, 377.
73. Fuchikami, T., Ohishi, K. and Ojiva, I. (1983) The Journal of Organic Chemistry, 48, 3803.
74. Pisano, C., Mezzetti, A. and Consiglio, G. (1992) Organometallics, 11, 20.
75. Consiglio, G. and Marchetti, M. (1976) Chimia, 30, 26.
76. Consiglio, G., Nefkens, S. C.A., Pisano, C. and Wenzinger, F. (1991) Helvetica Chimica Acta, 74, 323.
77. van Leeuwen, P.W.N.M., Zuideveld, M.A., Swennenhuis, B.H.G., Freixa, Z., Kamer, P. C.J., Goubitz, K., Fraanje, J., Lutz, M. and Spek, A.L. (2003) Journal of the American Chemical Society, 125, 5523.
78. del Ro, I., Ruiz, N. and Claver, C. (2000) Inorganic Chemistry Communications, 3, 166.
79. Sugi, Y. and Bando, K. (1976) Chemistry Letters, 727.
80. Guiu, E., Caporali, M., Muñoz, B., Müller, C., Lutz, M., Spek, A.L., Claver, C. and van Leeuwen, P.W.N.M. (2006) Organometallics, 25, 3102.
81. Zuidema, E., Bo, C. and van Leeuwen, P. W.N.M. (2007) Journal of the American Chemical Society, 129 (13), 3989.
82. Donald, S.M.A., Macgregor, S.A., Settels, V.D., Cole-Hamilton, J. and Eastham, G.R. (2007) Journal of the Chemical Society, Chemical Communications, 6, 562.
83. Botteghi, C., Consiglio, G. and Pino, P. (1973) Chimia, 27, 477.
84. Nozaki, K. and Ojima, I. (2000) Catalytic Asymmetric Synthesis (ed. I. Ojima), 2nd edn, John Wiley & Sons, Ltd, New York, p. 448.
85. Zhou, H., Hou, J., Cheng, J., Lu, S., Fu, H. and Wang, H. (1997) Journal of Organometallic Chemistry, 543, 227.
86. Zhou, H., Hou, J., Chen, J., Lu, S., Fu, H. and Wang, H. (1998) Chemistry Letters, 19 (3), 247.
87. del Ro, I., Ruiz, N., Claver, C., van der Veen, L.A. and van Leeuwen, P.W.N.M. (2000) Journal of Molecular Catalysis A: Chemical, 161, 39.
88. Miquel-Serrano, M.D., Aghmiz, A., Diéguez, M., Masdeu-Bultó, A.M., Claver, C. and Sinou, D. (1999) Tetrahedron: Asymmetry, 10, 4463.
89. Nozaki, K., Kantam, M.L., Horiuchi, T. and Takaya, H. (1997) Journal of Molecular Catalysis A: Chemical, 118, 247.
90. Girones, J., Duran, J., Polo, A. and Real, J. (2003) Journal of the Chemical Society, Chemical Communications, 1776.
91. Oi, S., Nomura, M., Aiko, T. and Inoue, Y. (1997) Journal of Molecular Catalysis A: Chemical, 115, 289.
92. Wang, L., Kwok, W. H., Chan, A.S.C., Tu, T., Hou, X. and Dai, L. (2003) Tetrahedron: Asymmetry, 14, 2291.
93. Godard, C., Ruiz, A. and Claver, C. (2006) Helvetica Chimica Acta, 89, 1610.
94. Chelucci, G., Cabras, M.A., Botteghi, C., Basoli, C. and Marchetti, M. (1996) Tetrahedron: Asymmetry, 7, 885.
95. Gotov, N. and Schmaltz, H.-G. (2001) Organic Letters, 3, 1753.
96. Cometti, G. and Chiusoli, G.P. (1982) Journal of Organometallic Chemistry, 236, C31.
97. Alper, H. and Hamel, N. (1990) Journal of the American Chemical Society, 112, 2803;
98. Alper, H. (1991) WO 9103452.
99. Yang, K. and Jiang, X. (2005) Chemical Journal on Internet, 7, 14.
100. Kawashima, Y., Okano, K., Nozaki, K. and Hiyama, T. (2004) Bulletin of the Chemical Society of Japan, 77, 347.
101. Muñoz, B., Marinetti, A., Ruiz, A., Castillon, S. and Claver, C. (2005) Inorganic Chemistry Communications, 8, 1113.
102. Kleeman, J. and Engel, A. (1982) Pharmazeutische Wirkstoffe, Thieme Verlag, Stuttgart.
103. Yoshikawa, K., Inoguchi, K. and Achiwa, K. (1990) Heterocycles, 31, 1413.
104. Ito, Y., Kamijo, T., Harada, H., Matsuda, F. and Terashima, S. (1990) Tetrahedron Letters, 2731.
105. Inoguchi, K., Morimoto, T. and Achiwa, K. (1989) Journal of Organometallic Chemistry, 370, C9.
106. Jendralla, H. (1991) Tetrahedron Letters, 32, 3671.
107. Kammermeier, B., Beck, G., Holla, W., Jacobi, D., Napierski, B. and Jendralla, H. (1996) Chemistry-A European Journal, 2, 307.
108. Nefkens, S.C.A., Sperrle, M. and Consiglio, G. (1993) Angewandte Chemie-International Edition in English, 2, 1719.
109. Hayashi, M., Takezaki, H., Hashimoto, Y., Takaoki, K. and Saigo, K. (1998) Tetrahedron Letters, 39, 7529.
110. Takeuchi, S., Ukaji, Y. and Inomata, K. (2001) Bulletin of the Chemical Society of Japan, 74, 955.
111. Sperrle, M. and Consiglio, G. (1999) Journal of Molecular Catalysis A: Chemical, 143, 263.
112. Wang, L., Kwok, W., Wu, J., Guo, R., Au-Yeung, T.T.-L., Zhou, Z., Chan, A.S.C. and Chan, K.-S. (2003) Journal of Molecular Catalysis A: Chemical, 196, 171.
113. Drent, E. (1984) EP 0106379;
114. Stephan, M.M. and Mohar, B. (2006) WO 2006136695;
115. Klosin, J., Whiteker, G. and Cobley, C. (2006) WO 2006116344;
116. Holz, J., Boermer, A., Almena, J.J., Kadyrov, R., Monsees, A. and Riermeier, T. (2006) WO 2006100169;
117. J., Boermer, A., Zayas, O., Almena Perea, J.J., Kadyrov, R., Monsees, A. and Riermeier, T. (2006) WO 2006100165;
118. Zhang, X. and Liu, D. (2005) WO 2005058917;
119. Zhang, X. and Tang, W. (2007) WO 2005117907;
120. Zhang, X. (2004) US 2004072680;
121. Zhang, X. and Tang, W. (2003) WO 2003042135;
122. Zhang, X. (2002) WO 2002040491;
123. Zhang, X. (2001) WO 2001034612;
124. Zhang, X. (2001) WO 2001021625;
125. Zhang, X. (1997) WO 9713763;
126. Alper, H. (1989) EP 305089;
127. Botteghi, C., Consiglio, G. and Pino, P. (1978) CH 598184;
128. Consiglio, G. (1977) CH 588438.