Progress in stereoselective catalysis by metal complexes with chiral ferrocenyl phosphines

Coordination Chemistry Reviews

Volumn 248, Issue 21-24, 2004, Pages 2131-2150

  Barbaro, Pierluigi ^a   Bianchini, Claudio ^a   Giambastiani, Giuliano ^a   Parisel, Sébastien L ^a  

^a CNR   (Italy)

Author keywords

(Z) methyl acetamidocinnamate; (Z) methylcinnamic acid; 1,3,5 cyclooctatriene; 1,5 cyclooctadiene; bicyclo 2.2.1 hepta 2,5 diene; COD; COT; cyclopentyl; Cyp; dimethyl itaconate; DMI; MAA; MAC; MCA; methyl 2 acetamidoacrylate; NBD; phobyl

Indexed keywords

ALCOHOL DERIVATIVE; ALKENE DERIVATIVE; ALLYL COMPOUND; FERROCENE DERIVATIVE; HYDROGEN; IMINE; KETONE DERIVATIVE; LIGAND; METAL COMPLEX; PHOSPHINE DERIVATIVE; PHOSPHORUS;

ALDOL REACTION; ALKYLATION; AMINATION; ATOM; CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROBORATION; HYDROFORMYLATION; HYDROGENATION; HYDROSILYLATION; REDUCTION; REVIEW; STEREOCHEMISTRY;

EID: 9744282662     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2004.03.022     Document Type: Review

References (168)

1. M.E. Davis, S.L. Suib (Eds.), Selectivity in Catalysis, ACS Symposium Series, vol. 517, American Chemical Society, Washington, 1993.
2. J.D. Morrison (Ed.), Asymmetric Synthesis, vol. 5, Academic Press, Orlando, FL, 1985.
3. B. Bosnich, M.D. Fryzuk, in: G.L. Geoffroy (Ed.), Topics in Inorganic and Organometallics Stereochemistry, Topics in Stereochemistry Series, vol. 12, Interscience Publications, New York, 1981.
4. Berrisford D.J., Bolm C., Sharpless K.B. Angew. Chem. Int. Ed. Engl. 34:1995;1059
5. R.E. Gawley, J. Aube, Principles of Asymmetric Synthesis, Pergamon, London, 1996.
6. Crosby J. Tetrahedron. 47:1991;4789
7. Stinson S.C. Chem. News Eng. 21:1998;83
8. Richards A., McCague R. Chem. Ind. June. 2:1997;422
9. Blaser H.U., Spindler F. Top. Catal. 4:1997;275
10. Stinson S.C. Chem. Eng. News. 41:1999;101
11. Stinson S.C. Chem. Eng. News. 43:2000;55
12. Stinson S.C. Chem. Eng. News. 40:2001;79
13. H.U. Blaser, B. Pugin, F. Spindler, in: B. Cornils, W.A. Herrmann (Eds.), Applied Homogeneous Catalysis by Organometallic Complexes, VCH, Weinheim, 1996.
14. R.A. Sheldon, Chirotechnology, Marcel Dekker Inc., New York, NY, 1993.
15. A.N. Collins, G.N. Sheldrake, J. Crosby (Eds.), Chirality in Industry, Wiley, New York, NY, 1992.
16. H.U. Blaser, Chem. Commun. (2003) 293.
17. I. Ojima (Ed.), Catalytic Asymmetric Synthesis, second ed., VCH Publishers, New York, 2000.
18. H. Brunner, W. Zettlmeier, Handbook of Enantioselective Catalysis with Transition Metal Compounds, vols. 1 and 2, VCH, Weinheim, 1993.
19. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
20. Tang W., Zhang X. Chem. Rev. 103:2003;3029
21. E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis, vols. 1-3, Springer, Berlin, 1999.
22. M.P. Doyle (Ed.), Advances in Catalytic Processes, vol. 1, JAI, London, 1995.
23. Blaser H.U., Malan C., Pugin B., Spindler F., Steiner H., Studer M. Adv. Synth. Catal. 345:2003;103
24. Jacobsen E.N. Acc. Chem. Res. 33:2000;421
25. Tye H., Comina P.J. J. Chem. Soc., Perkin Trans. 1:2001;1729
26. Burk M. Acc. Chem. Res. 33:2000;363
27. Ito Y., Sawamura M., Hayashi T. J. Am. Chem. Soc. 108:1986;6405
28. A. Togni, R. Häusel, Synlett (1990) 633.
29. Togni A., Rihs G., Blumer R.E. Organometallics. 11:1992;613
30. Togni A. Chimia. 50:1996;86
31. Sawamura M., Ito Y. Chem. Rev. 92:1992;857
32. Hayashi T. Pure Appl. Chem. 60:1988;7
33. Hayashi T., Kumada M. Acc. Chem. Res. 15:1982;395
34. Togni A. Angew. Chem. Int. Ed. Engl. 35:1996;1475
35. Stinson S.C. Chem. Eng. News. 38:1997;28
36. J. McGarrity, F. Spindler, R. Fuchs, M. Eyer, (LONZA AG), Eur. Pat. Appl. EP 624 587 A2, Chem. Abstr. 1995. 122, P81369q.
37. F. Spindler, B. Pugin, H.P. Jalett, H.P. Buser, U. Pittelkow, H.U. Blaser, in: R.E. Malz Jr. (Ed.), Catalysis of Organic Reactions (Chem. Ind.), vol. 68, Dekker, New York, 1996, pp. 153-166.
38. F. Spindler, B. Pugin, EP-A 0256982 (1988) (Ciba-Geigy AG).
39. Blaser H.U., Brieden W., Pugin B., Spindler F., Studer M., Togni A. Top. Catal. 19:2002;3
40. T. Hayashi, in: A. Togni, T. Hayashi (Eds.), Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science, VCH, Weinheim, 1995, pp. 105-142.
41. Colacot T.J. Chem. Rev. 103:2003;3101
42. Togni A., Venanzi L.M. Angew. Chem. Int. Ed. Engl. 33:1994;497
43. Togni A., Bieler N., Burckhardt U., Köllner C., Pioda G., Schneider R., Schnyder A. Pure Appl. Chem. 71:1999;1531
44. Richards C.J., Locke A. Tetrahedron: Asymmetry. 9:1998;2377
45. Dai L.X., Tu T., You S.L., Deng W.P., Hou X.L. Acc. Chem. Res. 36:2003;659
46. Whitesell J.K. Chem. Rev. 89:1989;1581
47. T. Hayashi, K. Yamamoto, M. Kumada, Tetrahedron Lett. (1974) 4405.
48. Hayashi T., Mise T., Fukushima M., Kagotani M., Nagashima N., Hamada Y., Matsumoto A., Kawakami S., Konishi M., Yamamoto K., Kumada M. Bull. Chem. Soc. Jpn. 53:1980;1138
49. K. Inoguchi, S. Sakuraba, K. Achiwa, Synlett (1992) 169.
50. Togni A., Breutel C., Schnyder A., Spindler F., Landert H., Tijani A. J. Am. Chem. Soc. 116:1994;4062
51. The Solvias-Josiphos ligands are patent-protected and are all produced by Solvias in technical quantities as either single ligands or ligand kits. See: http://www.ligands.solvias.com/data/html/all/enter_page.html. Family members are available in research quantities from Strem and Fluka.
52. B. Pugin, EP 0728768 (1996) (Ciba-Geigy).
53. B. Pugin, WO 96/32400 (1996) (Novartis).
54. B. Pugin, H. Landert, WO 98/01457 (1998) (Novartis).
55. E. Broger, Y. Crameri, P. Jones, WO 99/01453 (1997) (Hoffmann-La Roche).
56. Dobbs D.A., Vanhessche K.P.M., Brazi E., Rautenstrauch V., Lenoir J.Y., Genêt J.P., Wiles J., Bergens S.H. Angew. Chem. Int. Ed. Engl. 39:2000;1992
57. D.A. Dobbs, K.P.M. Vanhessche, V. Rautenstrauch, WO 98/52687 (1999) (Firmenich). Chem. Abstr. 130 (1999) 40076p.
58. V. Rautenstrauch, J.P. Genêt, J.Y. Lenoir, WO 97/18894 (1997) (Firmenich). Chem. Abstr. 127 (1997) 83071p.
59. Sturm T., Weissensteiner W., Spindler F., Mereiter K., López-Agenjo A.M., Manzano B.R., Jalón F.A. Organometallics. 21:2002;1766
60. G. Argouarch, O. Samuel, H.B. Kagan, Eur. J. Org. Chem. (2000) 2885.
61. Sturm T., Xiao L., Weissensteiner W. Chimia. 55:2001;688
62. The Walphos ligand family is produced in technical scale by Solvias and sold in research quantities by Strem.
63. Sturm T., Weissensteiner W., Spindler F. Adv. Synth. Catal. 345:2003;160
64. P. Herold, S. Stutz, WO 02/02500 A1 (2002) (Speedel Pharma AG).
65. Ireland T., Grossheimann G., Wieser-Jeunesse K., Knochel P. Angew. Chem. Int. Ed. Engl. 38:1999;3212
66. Lotz M., Polborn K., Knochel P. Angew. Chem. Int. Ed. Engl. 41:2002;4708
67. Ireland T., Tappe K., Grossheimann G., Knochel P. Chem. Eur. J. 8:2002;843
68. Kuwano R., Sawamura M., Okuda S., Asai T., Ito Y., Redon M., Krief A. Bull. Chem. Soc. Jpn. 70:1997;2807
69. Sawamura M., Kuwano R., Ito Y. J. Am. Chem. Soc. 117:1995;9602
70. Sawamura M., Hamashima H., Ito Y. J. Am. Chem. Soc. 114:1992;8295
71. Kuwano R., Okuda S., Ito Y. Tetrahedron: Asymmetry. 9:1998;2773
72. Kuwano R., Okuda S., Ito Y. J. Org. Chem. 63:1998;3499
73. Kuwano R., Sawamura M., Ito Y. Bull. Chem. Soc. Jpn. 73:2000;2571
74. Kuwano R., Ito Y. J. Org. Chem. 64:1999;1232
75. Kuwano R., Sato K., Kurokawa T., Karube D., Ito Y. J. Am. Chem. Soc. 122:2000;7614
76. Bianchini C., Barbaro P., Scapacci G., Farnetti E., Graziani M. Organometallics. 17:1998;3308
77. Rossen K., Pye P.J., DiMichele L.M., Volante R.P., Reider P.J. Tetrahedron Lett. 39:1998;6823
78. Klabe R.M., Bacheler L.T., Ala P.J., Erickson-Viitanen S., Meek J.L. Biochemistry. 37:1998;8735
79. Kuwano R., Sawamura M., Okuda S., Asai T., Ito Y., Redon M., Krief A. Bull. Chem. Soc. Jpn. 70:1997;2807
80. Marinetti A., Labrue F., Genêt J.P. Synlett. 12:1999;1975
81. Berens U., Burk M.J., Gerlach A., Hems W. Angew. Chem. Int. Ed. Engl. 39:2000;1981
82. The FerroTANE ligands are available from Chirotech Technology Ltd.
83. U. Berens, WO 99/24444 (Chirotech Technology Ltd.). Chem. Abstr. 130 (2000) 338253.
84. A. Marinetti, F. Labrue, B. Pons, S. Jus, L. Ricard, J.P. Genêt, Eur. J. Inorg. Chem. (2003) 2583.
85. Heller D., Drexler H.J., You J., Baumann W., Drauz K., Krimmer H.P., Börner A. Chem. Eur. J. 8:2002;5196
86. Liu D., Li W., Zhang X. Org. Lett. 4:2002;4471
87. M.T. Reetz, A. Gosberg, R. Goddard, S.H. Kyung, Chem. Commun. (1998) 2077.
88. Almena Perea J.J., Börner A., Knochel P. Tetrahedron Letters. 39:1998;8073
89. Kang J., Lee J.H., Ahn S.H., Choi J.S. Tetrahedron Lett. 39:1998;5523
90. Lotz M., Ireland T., Almena Perea J.J., Knochel P. Tetrahedron: Asymmetry. 10:1999;1839
91. Maienza F., Santoro F., Spindler F., Malan C., Mezzetti A. Tetrahedron: Asymmetry. 13:2002;1817
92. Maienza F., Wörle M., Steffanut P., Mezzetti A., Spindler F. Organometallics. 18:1999;1041
93. Nettekoven U., Kamer P.C.J., van Leeuwen P.W.N.M., Widhalm M., Spek A.L., Lutz M. J. Org. Chem. 64:1999;3996
94. Qiao S., Fu G.C. J. Org. Chem. 63:1998;4168
95. G. Argouarch, O. Samuel, O. Riant, J.C. Daran, H.B. Kagan, Eur. J. Org. Chem. (2000) 2893.
96. Boaz N.W., Debenham S.D., Mackenzie E.B., Large S.E. Org. Lett. 4:2002;2421
97. Oohara N., Katagiri K., Imamoto T. Tetrahedron: Asymmetry. 14:2003;2171
98. H.U. Blaser, B. Pugin, in: G.J. James, V. Dubois (Eds.), Chiral Reactions in Heterogeneous Catalysis, Plenum Press, New York, 1995.
99. D.E. De Vos, I.F.J. Vankelecom, P.A. Jacobs (Eds.), Chiral Catalyst Immobilization and Recycling, Wiley-VCH, Weinheim, 2000.
100. Bianchini C., Barbaro P. Top. Catal. 19:2002;17
101. R. Schneider, C. Köllner, I. Weber, A. Togni, Chem. Commun. (1999) 2415.
102. Köllner C., Pugin B., Togni A. J. Am. Chem. Soc. 120:1998;10274
103. Köllner C., Togni A. Can. J. Chem. 79:2001;1762
104. Chiba T., Miyashita A., Nohira H., Takaya H. Tetrahedron Lett. 34:1993;2351
105. Burk M., Harper G., Kalberg C. J. Am. Chem. Soc. 117:1995;4423
106. Ohkuma T., Koizumi M., Muñiz K., Hilt G., Kabuto C., Noyori R. J. Am. Chem. Soc. 124:2002;6508
107. Noyori R. Angew. Chem. Int. Ed. Engl. 41:2002;2008
108. C.G. Leong, O.M. Akotsi, M.J. Ferguson, S.H. Bergens, J.M. Brown, Chem. Commun. (2003) 750.
109. Xiao K., Mereiter F., Spindler W., Weissensteiner Tetrahedron: Asymmetry. 12:2001;1105
110. S. Kobayashi, H. Ishitani, Chem. Rev. (1999) 1069.
111. Bader R.R., Blaser H.U. Stud. Surf. Sci. Catal. 108:1997;17
112. Blaser H.U., Buser H.P., Coers K., Hanreich R., Jalett H.P., Jelsch E., Pugin B., Schneider H.D., Spindler F., Wegmann A. Chimia. 53:1999;275
113. H.U. Blaser, H.P. Buser, H.P. Jalett, B. Pugin, F. Spindler, Synlett (1999) 867.
114. B. Pugin, US 005783715, EP 0729969 A1 (1996) (Novartis).
115. Pugin B., Landert H., Spindler F., Blaser H.U. Adv. Synth. Catal. 344:2002;974
116. B. Pugin, WO 96/32400 (1996) (Novartis).
117. B. Pugin, WO 97/02232 (1997) (Ciba-Geigy AG).
118. Xiao D., Zhang X. Angew. Chem. Int. Ed. Engl. 40:2001;3425
119. Zassinovich G., Mestroni G., Gladiali S. Chem. Rev. 92:1992;1051
120. Jiang Y., Jiang Q., Zhu G., Zhang X. Tetrahedron Lett. 38:1997;215
121. Kitamura M., Tokunaga M., Ohkuma T., Noyori R. Org. Synth. 71:1993;1
122. Barbaro P., Bianchini C., Togni A. Organometallics. 16:1997;3004
123. P. Barbaro, C. Bianchini, G. Giambastiani, A. Togni, Eur. J. Inorg. Chem. (2003).
124. P. Barbaro, C. Bianchini, G. Giambastiani, A. Togni, Chem. Commun. (2002) 2672.
125. L.S. Hegedus, in: M. Schlosser (Ed), Organometallics in Synthesis, Wiley, Chichester, 1994, pp. 385-459 (Chapter 5)
126. J. Tsuji, Palladium Reagents and Catalysts, Innovation in Organic Synthesis, Wiley, Chichester, 1995
127. R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985
128. J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke, Principles and Applications of Organotransition Metal Chemistry, University Sciences Books, Mill Valley, CA, 1987
129. P.J. Harrington in: E.W. Abel, F.G.A. Stone, G. Wilkinson (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Pergamon, Oxford, UK, 1995, pp. 798-903 (Chapter 8.2)
130. Moreno-Mañas M., Pleixats R. Adv. Het. Chem. 66:1996;73
131. Heumann A., Réglier M. Tetrahedron. 51:1995;975
132. S.A. Godleski, in: I. Fleming, B.M. Trost (Eds), Comprehensive Organic Synthesis, vol. 4, Pergamon, Oxford, UK, 1991, pp. 585-661
133. Consiglio G., Waymouth M. Chem. Rev. 89:1989;257
134. J. Tsuji, H. Takahashi, M. Morikawa, Tetrahedron Lett. (1965) 4387.
135. L.S. Hegedus, Transition Metals in the Synthesis of Complex Molecules, University Science Books, Mill Valley, CA, 1994, pp. 261-305 (Chapter 9).
136. Trost B.M., Van Vranken D.L. Chem. Rev. 96:1996;395
137. Trost B.M. Acc. Chem. Res. 29:1996;355
138. Frost C.G., Howarth J., Williams J.M.J. Tetrahedron: Asymmetry. 3:1992;1089
139. J.M.J. Williams, Synlett (1996) 705.
140. Zhang W., Shimanuki T., Kida T., Nakatsuji Y., Ikeda I. J. Org. Chem. 64:1999;6247
141. Ganter C., Kaulen C., Englert U. Organometallics. 18:1999;5444. and references cited herein
142. Tanaka K., Qiao S., Tobisu M., Lo M.M.-C., Fu G.C. J. Am. Chem. Soc. 122:2000;9870. and references cited herein
143. Ogasawara M., Yoshida K., Hayashi T. Organometallics. 20:2001;3913
144. Nettekoven U., Widhalm M., Kamer P.C.J., van Leeuwen P.W.N. M. Tetrahedron: Asymmetry. 8:1997;3185
145. B.F.G. Johnson, S.A. Raynor, D.S. Shephard, T. Mashmeyer, J.M. Thomas, G. Sankar, S. Bromley, R. Oldroyd, L. Gladden, M.D. Mantle, Chem. Commun. (1999) 1167.
146. Kuwano R., Uemura T., Saitoh M., Ito Y. Tetrahedron Letters. 40:1999;1327
147. Tsuruta H., Imamoto T. Tetrahedron: Asymmetry. 10:1999;877
148. Lodberg Pedersen H., Johannsen M. J. Org. Chem. 67:2002;7982
149. C.H. Frohning, C.W. Kohlpaintner, in: B. Cornils, W. Herrmann (Eds.), Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996, p. 29.(b)
150. Ungváry F. Coord. Chem. Rev. 228:2002;61
151. Nettekoven U., Kamer P.C.J., Widhalm M., van Leeuwen P.W.N.M. Organometallics. 19:2000;4596
152. Rampf F.A., Herrmann W.A. J. Organomet. Chem. 601:2000;138
153. Sturm T., Weissensteiner W., Mereiter K., Kégl T., Jeges G., Petõlz G., Kollár L. J. Organomet. Chem. 595:2000;93
154. Müller T.E., Beller M. Chem. Rev. 98:1998;675
155. Giardello M.A., Conticello V.P., Brard L., Gagné M.R., Marks T.J. J. Am. Chem. Soc. 116:1994;10241
156. Li Y.W., Marks T.J. Organometallics. 15:1996;3770
157. Tian S., Arredondo V.M., Stern C.L., Marks T.J. Organometallics. 18:1999;2568
158. Douglass M.R., Ogasawara M., Hong S., Metz M.V., Marks T.J. Organometallics. 21:2002;283. and references within
159. Ackermann L., Bergman R.G. Org. Lett. 4:2002;1475
160. Johnson J.S., Bergman R.G. J. Am. Chem. Soc. 123:2001;2923
161. Fairfax D., Stein M., Livinghouse T., Jensen M. Organometallics. 16:1997;1523
162. Kim Y.K., Livinghouse T., Bercaw J.E. Tetrahedron Lett. 42:2001;2933
163. Haak E., Bytschkov I., Doye S. Angew. Chem. Int. Ed. Engl. 38:1999;3389
164. Heutling A., Doye S. J. Org. Chem. 67:2002;1961. and references within
165. Dorta R., Egli P., Zürcher F., Togni A. J. Am. Chem. Soc. 119:1997;10857
166. L. Fadini, A. Togni, Chem. Commun. (2003) 30.
167. R. Kuwano, H. Miyazaki, Y. Ito, Chem. Commun. (1998) 71.
168. Colby E.A., Jamison T.F. J. Org. Chem. 68:2003;156