Mechanism of Enantioselective Hydrogenation

The Handbook of Homogeneous Hydrogenation

Volumn , Issue , 2008, Pages 1073-1103

  Brown, John M ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

Dehydroamino acid; Discovery; Kinetic study; Mono alkene; Synthesis

Indexed keywords

EID: 84891011808     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527619382.ch31     Document Type: Chapter

References (160)

1. Osborn, J.A., Jardine, F.H., Young, G.W., Wilkinson, G., J. Chem. Soc. A, 1966, 1711.
2. Horner, L., Winkler, H., Annalen, 1965, 685, 1;
3. Horner, L., Balzer, W.D., Peterson, D.J., Tetrahedron Lett., 1966, 3315;
4. Korpiun, O., Mislow, K., J. Am. Chem. Soc., 1967, 89, 4784;
5. Korpiun, O., Lewis, R.A., Chickos, J., Mislow, K., J. Am. Chem. Soc., 1968, 90, 4842;
6. Naumann, K., Zon, G., Mislow, K., J. Am. Chem. Soc, 1969, 91, 7012.
7. Horner, L., Siegel, H., Buethe, H., Angew. Chem., Int. Ed., 1968, 7, 942.
8. Knowles, W. S., Sabacky, M.J., Chem. Commun., 1968, 1445.
9. Kagan, H.B., Dang, T.P., J. Am. Chem. Soc, 1972, 94, 6429.
10. Vineyard, B.D., Knowles, W. S., Sabacky, M.J., Bachman, G.L., Weinkauff, D.J., J. Am. Chem. Soc., 1977, 99, 5946.
11. Chaloner, P.A., Esteruelas, M.A., Joo, F., Oro, L. A., Homogeneous Hydrogenation, Kluwer, Dordrecht, 1994;
12. Noyori, R., Asymmetric Catalysis in Organic Synthesis (especially Chapter 2), John Wiley & Sons, Inc., New York, 1994;
13. Ojima, I. (Ed.), Catalytic Asymmetric Synthesis, John Wiley & Sons, Inc., New York, 2000.
14. Hallman, P.S., Evans, D., Osborn, J.A., Wilkinson, G., Chem. Commun., 1967, 305;
15. Hallman, P.S., McGarvey, B.R., Wilkinson, G., J. Chem. Soc. A, 1968, 3143;
16. Rose, D., Gilbert, J. D., Richardson, R.P., Wilkinson, G., J. Chem. Soc. A, 1969, 2610.
17. Crabtree, R.H., Felkin, H., Morris, G.E., Chem. Commun., 1976, 716;
18. Crabtree, R.H., Felkin, H., Morris, G.E., J. Organomet. Chem., 1977, 141, 205.
19. Noyori, R., Ohta, M., Hsiao, Y., Kita-mura, M., Ohta, T., Takaya, H., J. Am. Chem. Soc, 1986, 108, 7117;
20. Takaya, H., Ohta, T., Sayo, N., Kumobayashi, H., Akutagawa, S., Inoue, S., Kasahara, I., Noyori, R., J. Am. Chem. Soc., 1987, 109, 1596;
21. Ohta, T., Takaya, H., Kitamura, M., Nagai, K., Noyori, R., J. Org. Chem., 1987, 52, 3174.
22. Kitamura, M., Ohkuma, T., Inoue, S., Sayo, N., Kumobayashi, H., Akutagawa, S., Ohta, T., Takaya, H., Noyori, R., J. Am. Chem. Soc., 1988, 110, 629;
23. Noyori, R., Ohkuma, T., Kitamura, M., Takaya, H., Sayo, N., Kumobayashi, H., Akutagawa, S., J. Am. Chem. Soc., 1987, 109, 5856.
24. Lightfoot, A., Schnider, P., Pfaltz, A., Angew. Chem., Int. Ed., 1998, 37, 2897.
25. Blaser, H.-U., Schmidt, E. (Eds.), Asymmetric Catalysis on an Industrial Scale; Challenges, Approaches and Solutions. Wiley-VCH, New York, 2004.
26. Brown, J.M., in: Jacobsen, E.N., Pfaltz, A., Yamamoto, H. (Eds.), Comprehensive Asymmetric Catalysis, Volume I, Chapter 5.1. Springer, Berlin, 1999, pp. 121.
27. Landis, C. R., Halpern, J., J. Am. Chem. Soc., 1987, 109, 1746;
28. Halpern, J., Science, 1982, 217, 401;
29. Halpern, J., Chan, A. S. C., J. Am. Chem. Soc., 1980, 102, 838;
30. Chan, A.S.C., Pluth, J.J., Halpern, J., J. Am. Chem. Soc., 1980, 102, 5952;
31. Sun, Y.K., Landau, R.N., Wang, J., Leblond, C., Blackmond, D.G., J. Am. Chem. Soc., 1996, 118, 1348.
32. Brown, J.M., Chaloner, P.A., Nicholson, P.N., J. Chem. Soc., Chem. Commun, 1978, 646;
33. Brown, J.M., Chaloner, P.A., Tetrahedron Lett., 1978, 1877;
34. Brown, J.M., Chaloner, P.A., J. Chem. Soc., Chem. Commun., 1978, 321;
35. Brown, J.M., Chaloner, P.A., Descotes, G., Glaser, R., Lafont, D., Sinou, D., J. Chem. Soc., Chem. Commun., 1979, 611;
36. Brown, J.M., Chaloner, P.A., J. Chem. Soc., Chem. Commun., 1979, 613;
37. Brown, J.M., Chaloner, P.A., J. Chem. Soc., Chem. Commun., 1980, 344;
38. Brown, J. M., Chaloner, P. A., Glaser, R., Geresh, S., Tetrahedron, 1980, 36, 815;
39. Descotes, G., Lafont, D., Sinou, D., Brown, J.M., Chaloner, P. A., Parker, D., New J. Chem., 1981, 5, 167.
40. Drexler, H.-J., Baumann, W., Spannenberg, A., Fischer, C., Heller, D., J. Orga-nometal. Chem., 2001, 621, 89;
41. Borner, A., Heller, D., Tetrahedron Lett., 2001, 42, 223;
42. Braun, W., Salzer, A., Drexler, H.-J., Spannenberg, A., Heller, D., Dalton Trans. 2003, 1606.
43. Brown, J.M., Canning, L. R., Downs, A. J., Forster, A. M., J. Organomet. Chem., 1983, 255, 103.
44. Brown, J. M., Chaloner, P. A., Parker, D., Adv. Chem. Ser., 1982, 196, 355.
45. Brown, J. M., Chaloner, P. A., Morris, G. A., J. Chem. Soc. Chem. Commun., 1983, 664;
46. Brown, J.M., Chaloner, P.A., Morris, G.A., J. Chem. Soc. Perkin Trans. 2, 1987, 1583;
47. Ramsden, J.A., Claridge, T. D.W., Brown, J.M., J. Chem. Soc. Chem. Commun., 1995, 2469.
48. Burk, M.J., Feaster, J.E., Nugent, W.A., Harlow, R. L., J. Am. Chem. Soc., 1993, 115, 10125.
49. Muci, A. R., Campos, K.R., Evans, D.A., J. Am. Chem. Soc., 1995, 117, 9075.
50. Imamoto, T., Watanabe, J., Wada, Y., Ma-suda, H., Yamada, H., Tsuruta, H., Mat-sukawa, S., Yamaguchi, K., J. Am. Chem. Soc., 1998, 120, 1635;
51. Miura, T., Imamoto, T., Tetrahedron Lett, 1999, 40, 4833;
52. Gridnev, I. D., Yamanoi, Y., Higashi, N., Tsuruta, H., Yasutake, M., Imamoto, T., Adv. Synth. Catal., 2001, 343, 118;
53. Gridnev, I.D., Yasutake, M., Higashi, N., Im-amoto, T., J. Am. Chem. Soc., 2001, 123, 5268;
54. Imamoto, T., Pure Appl. Chem., 2001, 73, 373;
55. Ohashi, A., Imamoto, T., Tetrahedron Lett., 2001, 42, 1099;
56. Yasutake, M., Gridnev, I.D., Higashi, N., Imamoto, T., Org. Lett., 2001, 3, 1701;
57. Ohashi, A., Kikuchi, S., Yasutake, M., Imamoto, T., Eur. J. Org. Chem., 2002, 2535;
58. Crepy, K.V. L., Imamoto, T., Adv. Synth. Catal., 2003, 345, 79;
59. Oohara, N., Katagiri, K., Imamoto, T., Tetrahedron: Asymmetry, 2003, 14, 2171.
60. Pye, P. J., Rossen, K., Reamer, R. A., Tsou, N. N., Volante, R. P., Reider, P. J., J. Am. Chem. Soc., 1997, 119, 6207;
61. Ros-sen, K., Pye, P.J., DiMichele, L. M., Volante, R.P., Reider, P.J., Tetrahedron Lett., 1998, 39, 6823.
62. Tang, W.J., Zhang, X.M., Chem. Rev., 2003, 103, 3029.
63. Claver, C., Fernandez, E., Gillon, A., Heslop, K., Hyett, D.J., Martorell, A., Orpen, A.G., Pringle, P. G., Chem. Commun., 2000, 961;
64. Reetz, M.T., Sell, T., Tetrahedron Lett, 2000, 41, 6333;
65. van den Berg, M., Minnaard, A. J., Schudde, E.P., van Esch, J., de Vries, A. H.M., de Vries, J.G., Feringa, B.L., J. Am. Chem. Soc., 2000, 122, 11539;
66. van den Berg, M., Haak, R.M., Minnaard, A. J., De Vries, A. H.M., De Vries, J.G., Feringa, B.L., Adv. Synth. Catal., 2002, 344, 1003.
67. Gridnev, I.D., Higashi, N., Asakura, K., Imamoto, T., J. Am. Chem. Soc., 2000, 122, 7183.
68. Gridnev, I.D., Higashi, N., Imamoto, T., Organometallics, 2001, 20, 4542.
69. Gridnev, I.D., Yamanoi, Y., Higashi, N., Tsuruta, H., Yasutake, M., Imamoto, T., Adv. Synth. Catal., 2001, 343, 118;
70. Grid-nev, I.D., Imamoto, T., Organometallics, 2001, 20, 545.
71. Heinrich, H., Giernoth, R., Bargon, J., Brown, J. M., Chem. Commun., 2001, 1296.
72. Halpern, J., Wong, C.S., J. Chem. Soc., Chem. Commun., 1973, 629.
73. Brown, J. M., Parker, D., Organometallics, 1982, 1, 950.
74. Burk, M.J., Casy, G., Johnson, N.B., J. Org. Chem., 1998, 63, 6084.
75. Gridnev, I.D., Higashi, N., Imamoto, T., J. Am. Chem. Soc., 2000, 122, 10486.
76. Feldgus, S., Landis, C.R., Organometallics, 2001, 20, 2374.
77. Harthun, A., Kadyrov, R., Selke, R., Bargon, J., Angew. Chem, Int. Ed. Engl., 1997, 36, 1103.
78. Giernoth, R., Heinrich, H., Adams, N.J., Deeth, R.J., Bargon, J., Brown, J. M., J. Am. Chem. Soc, 2000, 122, 12381.
79. Samuel, O., Couffignal, R., Lauer, M., Zhang, S. Y., Kagan, H.B., Nouv. J. Chim., 1981, 5, 15
80. see also: Fryzuk, M.D., Bosnich, B., J. Am. Chem. Soc, 1977, 99, 6262;
81. Pavlov, V.A., Klabunovs-kii, E. I., Struchkov, Y.T., Voloboev, A.A., Yanovsky, A. I., J. Mol. Catal., 1988, 44, 217.
82. Kyba, E. P., Davis, R. E., Juri, P.N., Shirley, K. R., Inorg. Chem. 1981, 20, 3616.
83. Knowles, W. S., Accounts Chem. Res., 1983, 16, 106.
84. Marinetti, A., Jus, S., Genet, J.P., Tetrahedron Lett., 1999, 40, 8365.
85. Gridnev, I.D., Imamoto, T., Accounts Chem. Res., 2004, 37, 633.
86. Drexler, H.J., Zhang, S.L., Sun, A.L., Spannenberg, A., Arrieta, A., Preetz, A., Heller, D., Tetrahedron: Asymmetry, 2004, 15, 2139.
87. Landis, C.R., Hilfenhaus, P., Feldgus, S., J. Am. Chem. Soc, 1999, 121, 8741.
88. Feldgus, S., Landis, C. R., J. Am. Chem. Soc., 2000, 122, 12714.
89. Ramsden, J.A., Claridge, T., Brown, J.M., J. Chem. Soc. Chem. Commun., 1995, 2469, and references therein.
90. Li, M., Tang, D., Luo, X., Shen, W., Int. J. Quantum Chem, 2005, 102, 53.
91. Knowles, W. S., Sabacky, M.J., Vineyard, B. D., J. Chem. Soc. Chem. Commun., 1972, 10.
92. Guillen, F., Fiaud, J.-C., Tetrahedron Lett., 1999, 40, 2939;
93. Guillen, F., Rivard, M., Toffano, M., Legros, J.-Y., Daran, J.-C., Tetrahedron, 2002, 58, 5895;
94. Fiaud, J.-C., Dobrota, C., Toffano, M., Fiaud, J.-C., Tetrahedron Lett., 2004, 45, 8153.
95. Bernsmann, H., van den Berg, M., Hoen, R., Minnaard, A.J., Mehler, G., Reetz, M.T., De Vries, J.G., Feringa, B.L., J. Org. Chem, 2005, 70, 943.
96. Hoen, R., van den Berg, M., Bernsmann, H., Minnaard, A.J., de Vries, J. G., Feringa, B.L., Org. Lett, 2004, 6, 1433, and references therein.
97. van den Berg, M., et al., Adv. Synth. Catal., 2003, 345, 308.
98. Reetz, M. T., Mehler, G., Tetrahedron Lett., 2003, 44, 4593;
99. Reetz, M.T., Mehler, G., Melswinkel, A., Sell, T., Tetrahedron: Asymmetry, 2004, 15, 3483;
100. Reetz, M.T., Li, X., Angew. Chem., Int. Ed., 2005, 44, 2959.
101. Wu, H.P., Hoge, G., Org. Lett., 2004, 6, 3645;
102. Reetz, M.T., Li, X.G., Tetrahedron, 2004, 60, 9709;
103. Jerphagnon, T., Renaud, J.L., Demonchaux, P., Ferreira, A., Bru-neau, C., Adv. Synth. Catal., 2004, 346, 33;
104. Huang, H.M., Liu, X.C., Chen, S., Chen, H.L., Zheng, Z., Tetrahedron: Asymmetry, 2004, 15, 2011;
105. Hsiao, Y., et al., J. Am. Chem. Soc, 2004, 126, 9918;
106. Hoge, G., Samas, B., Tetrahedron: Asymmetry, 2004, 15, 2155;
107. Tang, W., Wu, S., Zhang, X., J. Am. Chem. Soc., 2003, 125, 9570;
108. Tang, W., Wang, W., Chi, Y., Zhang, X., Angew. Chem.-Int. Ed., 2003, 42, 3509;
109. Tang, W., Zhang, X., Org. Lett., 2002, 4, 4159;
110. Pena, D., Minnaard, A.J., de Vries, J.G., Feringa, B.L., J. Am. Chem. Soc., 2002, 124, 14552;
111. Yasutake, M., Gridnev, I.D., Higa-shi, N., Imamoto, T., Org. Lett., 2001, 3, 1701;
112. Zhu, G., Chen, Z., Zhang, X., J. Org. Chem, 1999, 64, 6907;
113. Zhu, G., Casalnuovo, A. L., Zhang, X., J. Org. Chem., 1998, 63, 8100.
114. Heller, D., Holz, J., Komarov, I., Drexler, H.-J., You, J., Drauz, K., Borner, A., Tetrahedron: Asymmetry, 2002, 13, 2735;
115. Heller, D., Drexler, H.-J., You, J., Baumann, W., Drauz, K., Krimmer, H.-P., Borner, A., Chem. Eur. J., 2002, 8, 5196.
116. Drexler, H.-J., Baumann, W., Schmidt, T., Zhang, S., Sun, A., Spannenberg, A., Fischer, C., Buschmann, H., Heller, D., Angew. Chem., Int. Ed., 2005, 44, 1184.
117. Yasutake, M., Gridnev, I.D., Higashi, N., Imamoto, T., Org. Lett., 2001, 3, 1701.
118. Evans, D.A., Michael, F.E., Tedrow, J.S., Campos, K. R., J. Am. Chem. Soc., 2003, 125, 3534.
119. Drexler, H.J., You, J.S., Zhang, S.L., Fischer, C., Baumann, W., Spannenberg, A., Heller, D., Org. Process Res. Dev., 2003, 7, 355.
120. Tang, W.J., Wu, S.L., Zhang, X.M., J. Am. Chem. Soc., 2003, 125, 9570.
121. Brown, J.M., Maddox, P.J., Chem. Com-mun., 1987, 1278.
122. Brown, J.M., J. Organomet. Chem, 2004, 689, 4006.
123. Wiles, J. A., Bergens, S. H., Vanhessche, K. P. M., Dobbs, D. A., Rautenstrauch, V., Angew. Chem.-Int. Ed., 2001, 40, 914;
124. Wiles, J.A., Daley, C.J.A., Hamilton, R.J., Leong, C.G., Bergens, S.H., Organometallics, 2004, 23, 4564.
125. Wiles, J. A., Bergens, S. H., Organometal-lics, 1999, 18, 3709;
126. Wiles, J.A., Bergens, S.H., Organometallics, 1998, 17, 2228;
127. Wiles, J. A., Bergens, S. H., Young, V. G., J. Am. Chem. Soc., 1997, 119, 2940.
128. Kitamura, M., Tsukamoto, M., Bessho, Y., Yoshimura, M., Kobs, U., Widhalm, M., Noyori, R., J. Am. Chem. Soc., 2002, 124, 6649.
129. Ohta, T., Takaya, H., Noyori, R., Tetrahedron Lett, 1990, 31, 7189.
130. Crabtree, R.H., Davis, M.W., Organome-tallics, 1983, 2, 681;
131. Crabtree, R.H., Davis, M.W., J. Org. Chem., 1986, 51, 2655.
132. Examples include: Kaellstroem, K., Hedberg, C., Brandt, P., Bayer, A., Andersson, P.G., J. Am. Chem. Soc., 2004, 126, 14308;
133. Trifonova, A., Diesen, J. S., Chapman, C.J., Andersson, P. G., Org. Lett., 2004, 6, 3825;
134. Smidt, S. P., Menges, F., Pfaltz, A., Org. Lett., 2004, 6, 2023;
135. Liu, D., Tang, W., Zhang, X., Org. Lett., 2004, 6, 513;
136. Schenkel, L. B., Ellman, J.A., J. Org. Chem., 2004, 69, 1800-1802;
137. Drury, W. J., Zimmermann, N., Keenan, M., Hayashi, M., Kaiser, S., Goddard, R., Pfaltz, A., Angew. Chem.-Int. Ed., 2004, 43, 70;
138. Mazet, C., Smidt, S. P., Meuwly, M., Pfaltz, A., J. Am. Chem. Soc., 2004, 126, 14176;
139. Perry, M.C., Cui, X.H., Powell, M.T., Hou, D.R., Reibenspies, J. H., Burgess, K., J. Am. Chem. Soc., 2003, 125, 113;
140. Menges, F., Pfaltz, A., Adv. Synth. Catal., 2002, 344, 40-44;
141. Coz-zi, P. G., Zimmermann, N., Hilgraf, R., Schaffner, S., Pfaltz, A., Adv. Synth. Catal., 2001, 343, 450;
142. Blankenstein, J., Pfaltz, A., Angew. Chem.-Int. Ed., 2001, 40, 4445.
143. Crabtree, R.H., Felkin, H., Morris, G.E., J. Organomet. Chem., 1977, 141, 205;
144. Crabtree, R.H., Felkin, H., Khan, T., Morris, G.E., J. Organomet. Chem., 1978, 144, C15;
145. Crabtree, R.H., Felkin, H., Fil-lebeen-Khan, T., Morris, G. E., J. Organo-met. Chem., 1979, 168, 183.
146. Mazet, C., Smidt, S. P., Meuwly, M., Pfaltz, A., J. Am. Chem. Soc., 2004, 126, 14176.
147. Brandt, P., Hedberg, C., Andersson, P.G., Chem.-Eur. J, 2003, 9, 339.
148. Dietiker, R., Chen, P., Angew. Chem., Int. Ed., 2004, 43, 5513.
149. Blackmond, D.G., Lightfoot, A., Pfaltz, A., Rosner, T., Schnider, P., Zimmerman, N., Chirality, 2000, 12, 442.
150. Buriak, J. M., Klein, J. C., Herrington, D.G., Osborn, J.A., Chem. Eur. J., 2000, 6, 139.
151. Smidt, S. P., Pfaltz, A., Martinez-Vi-viente, E., Pregosin, P. S., Albinati, A., Organometallics, 2003, 22, 1000.
152. Macchioni, A., Eur. J. Inorg. Chem., 2003, 195;
153. Macchioni, A., Chem. Rev., 2005, 105, 2039;
154. Drago, D., Pregosin, P.S., Pfaltz, A., Chem. Commun., 2002, 286;
155. Martinez-Viviente, E., Pregosin, P.S., In-org. Chem., 2003, 42, 2209;
156. Martinez-Vi-viente, E., Pregosin, P. S., Vial, L., Herse, C., Lacour, J., Chem. Eur. J., 2004, 10, 2912;
157. Pregosin, P. S., Martinez-Viviente, E., Kumar, P. G.A., J. Chem. Soc. Dalton Trans., 2003, 4007.
158. Smidt, S. P., Zimmermann, N., Studer, M., Pfaltz, A., Chem.-Eur. J., 2004, 10, 4685.
159. Cui, X., Ogle, J.W., Burgess, K., Chem. Commun., 2005, 672;
160. Cui, X., Burgess, K., J. Am. Chem. Soc., 2003, 125, 14212.