Chiral ferrocenylthiazolidines, new ligands for palladium complexes

Journal of Organometallic Chemistry

Volumn 637-639, Issue , 2001, Pages 116-125

  González, Asensio ^a   Granell, Jaume R ^a   López, Concepción ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Chiral; Ferrocene; Palladium; S donor; Thiazolidines

Indexed keywords

EID: 0035803789     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(01)00880-4     Document Type: Article

References (102)

1. Ojima I. Catalytic Asymmetric Synthesis. 1993;VCH, Cambridge.
2. Noyori R. Asymmetric Catalysis in Organic Synthesis. 1994;Wiley, New York.
3. Gawley R.E., Aube J. Principles of Asymmetric Synthesis. 1996;Pergamon, Oxford.
4. Evans D.A., Kozlowski M.C., Murry J.A., Burgey C.S., Campos K.R., Connell B.T., Staples R.J. J. Am. Chem. Soc. 121:1999;669.
5. Evans D.A., Burgey C.S., Kozlowski M.C., Tregay S.W. J. Am. Chem. Soc. 121:1999;686.
6. Evans D.A., Olhava E.J., Johnson J.S., Janey J.M. Angew. Chem. Int. Ed. Engl. 37:1999;3372.
7. Evans D.A., Rovis T., Kozlowski M.C., Tedrow J.S. J. Am. Chem. Soc. 121:1999;1994.
8. Cheluchi G., Deriu S., Pinna G.A., Saba A., Valenti R. Tetrahedron: Asymmetry. 10:1999;3803.
9. Nordström K., Macedo E., Moberg C. J. Org. Chem. 62:1997;1604.
10. Brunner H., Becker R., Riepl G. Organometallics. 3:1984;1354.
11. Ojima I., Clos N., Bastos C. Tetrahedron. 45:1989;6901.
12. Blaser H.U. Chem. Rev. 92:1992;935.
13. Coppola G.M., Shuster H.F. Asymmetric Synthesis. 1987;Wiley, New York.
14. Braga A.L., Appelt H.R., Schneider P.H., Silveira C.C., Wessjohann L.A. Tetrahedron: Asymmetry. 10:1999;1733.
15. Kossenjans M., Martens J. Tetrahedron: Asymmetry. 9:1998;1409.
16. Xingshu L., Rugang X. Tetrahedron: Asymmetry. 7:1996;2779.
17. Christoffers J., Mann A., Pickardt J. Tetrahedron. 55:1999;5377.
18. Togni A., Hayashi T. Ferrocenes, Homogeneous Catalysis, Organic Synthesis and Material Science. 1993;VCH, Weinheim.
19. Richards C.J., Locke A.J. Tetrahedron: Asymmetry. 9:1998;2377.
20. Song J.H., Cho D.J., Jeon J.H. Inorg. Chem. 38:1999;893.
21. Cayuela E.M., Xiao L., Sturm T., Manzano B.R., Jalon F.A., Weissensteiner W. Tetrahedron: Asymmetry. 11:2000;861.
22. Gotov B., Toma S., Solcániová E., Cvengros J. Tetrahedron. 56:2000;671.
23. Wild S.B. Coord. Chem. Rev. 166:1997;291.
24. Robin F., Mercier F., Ricard L., Mathey F., Spagnol M. Chem. Eur. J. 8:1997;1365.
25. Dunina V.V., Golovan F.B. Tetrahedron: Asymmetry. 6:1995;2747.
26. Leung P., Quek G.H., Lang H., Liu A.M., Mok K.F., White A.J., Williams D.J., Rees N., McFarlane W. J. Chem. Soc. Dalton Trans. 1998;1639.
27. Barclay C.E., Deeble G., Doyle R.J., Elix S.A., Salem G., Jones T.L., Wild S.B., Willis A.C. J. Chem. Soc. Dalton Trans. 1995;57.
28. Pabel M., Willis A.C., Wild S.B. Inorg. Chem. 35:1996;1244.
29. Berens U., Brown J.M., Long J., Selke R. Tetrahedron: Asymmetry. 7:1996;285.
30. Chelucci G., Cabras M.A., Saba A., Sechi A. Tetrahedron: Asymmetry. 7:1996;1027.
31. Gladiali S., Dore A., Fabbri D., De Lucci O., Manassero M. Tetrahedron: Asymmetry. 5:1994;511.
32. Chooi S.Y.M., Tan M.K., Leung P., Mok K.F. Inorg. Chem. 33:1994;3096.
33. Pabel M., Willis A.C., Wild S.B. Tetrahedron: Asymmetry. 6:1995;2369.
34. He G., Mok K.F., Leung P.H. Organometallics. 18:1999;4027.
35. López C., Bosque R., Sainz D., Solans X., Font-Bardía M. Organometallics. 16:1997;3261.
36. Albert J., Cadena J.M., Granell J., Muller G., Ordinas J.I., Panyella D., Puerta C., Sañudo C., Valerga P. Organometallics. 17:1999;3513.
37. Dunina V.V., Razmuyslova E.D., Kuz'mina L.G., Churakov A.V., Rubina M.Y., Grishin Y.K. Tetrahedron: Asymmetry. 10:1999;3147.
38. Albert J., Granell J., Minguez J., Muller G., Sainz D., Valerga P. Organometallics. 16:1997;3561.
39. Dunina V.V., Kuz'mina L.G., Yu Rubina M., Grishin Y.K., Veits Y.A., Kazakova E.I. Tetrahedron: Asymmetry. 10:1999;1483.
40. Albert J., Cadena J.M., Delgado S., Granell J. J. Organomet. Chem. 603:2000;235.
41. Albert J., Cadena J.M., Granell J., Solans X., Font-Bardía M. Tetrahedron: Asymmetry. 11:2000;1943.
42. Albert J., Cadena J.M., Granell J., Muller G., Panyella D., Sañudo C. Eur. J. I. Chem. 2000;1283.
43. Hermann W.A., Cornils B. Angew. Chem. Int. Ed. Engl. 36:1997;1049.
44. Kagan H.B. Morrison. Asymmetric Synthesis. 5:1985;Academic Press, Orlando. (chap. 1).
45. Jolly P.W., Wilke G. Hermann W.A., Cornils B. Applied Homogeneous Catalysis with Organometallic Compounds. 1996;VCH, Weinheim.
46. Omae I. Applications of Organometallic Compounds. 1998;Wiley, Chichester.
47. You S.L., Hou X.L., Dai L.X. Tetrahedron: Asymmetry. 11:2000;1495.
48. Imai Y., Zhang W., Kida T., Nakatsuji Y., Ikeda I. Chem. Lett. 1999;243.
49. Ahn K.H., Cho C.W., Park J., Lee S. Tetrahedron: Asymmetry. 8:1997;1179.
50. Zhang W., Hirao T., Ikeda I. Tetrahedron Lett. 37:1996;4545.
51. Canal J.M., Gómez M., Jiménez F., Rocamora M., Muller G., Duñach E., Franco D., Jimenez A., Cano F.H. Organometallics. 19:2000;966.
52. Gómez M., Jansat S., Muller G., Panyella D., van Leuwen P.W.N.M., Kramer P.C.J., Goubitz K., Fraonje J. Organometallics. 18:1999;4970.
53. Gómez M., Muller G., Panyella D., Rocamora M., Clinet J., Duñach E., Franco D. Organometallics. 16:1997;5900.
54. Cheney A., Bryce M.R., Chubb R.W.J., Batsanov A.S., Howard J.A.K. Tetrahedron: Asymmetry. 8:1997;2337.
55. Confalone P.N., Pizzolato G., Baggiolini E., Lollar D., Uskokovic M. J. Am. Chem. Soc. 99:1977;7020.
56. Szilágyi L., Györgydeák Z. J. Am. Chem. Soc. 101:1979;427.
57. S. Díaz, A. González, Synth. Commun. (2001) in press.
58. Gmelin Handbuch der Anorganische Chemie, Eisen Organische Verbindungen, Springer, A4-A10, Heildelberg, 1989.
59. Szafran Z., Pike R.M., Singh M.M. Microscale Inorganic Chemistry. A Comprenhensive Laboratory Experience. 1991;Wiley, New York. (p. 298).
60. Lindley J. J. Chem. Educ. 57:1980;671.
61. Bailey C.T., Lisensky G.C. J. Chem. Educ. 62:1985;896.
62. Zanello P., Cinquantini A., Mangani S., Opromolla G., Pardi L., Janiak C., Raush M.S.D. J. Organomet. Chem. 471:1994;171.
63. Zanello P., Opromolla G., Pardi L., Pannell K.H., Sharma K.H. J. Organomet. Chem. 450:1993;193.
64. Blom N.F., Neuse E.W., Thomas M.G. Transition Met. Chem. 12:1987;301.
65. Little W.F., Reilly C.N., Johnson J.D., Sanders A.P. J. Am. Chem. Soc. 86:1964;1382.
66. Hoh G.L., Mc Ewen W.F., Kleinberg J. J. Am. Chem. Soc. 83:1961;3949.
67. Maitlis P.M., Espinet P., Russell M.J.H. Wilkinson G., Stone F.G.A., Abel E.W. Comprenhensive Organometallic Chemistry. 6:1982;Pergamon Press, Oxford. (chap. 38, p. 411).
68. Elguero J., Fruchier A., De la Hoz A., Jalon F., Manzano B., Otero A., Gómez de la Torre F. Chem. Ber. 129:1996;384.
69. Crociani B., Antomaroli S., Paci M. Organometallics. 16:1997;384.
70. Pregosin P.S., Trabesinger G. J. Chem. Soc. Dalton Trans. 1998;727.
71. Golloll A., Örnebro J., Grennberg H., Bäckvall J.E. J. Am. Chem. Soc. 116:1994;3631.
72. Ankersmit H.A., Løken B., Kooijman H., Spek A., Vrieze K., van Koten G. Inorg. Chim. Acta. 252:1996;141.
73. Albinati A., Kunz R.W., Amman C.J., Pregosin P.S. Organometallics. 10:1991;1800.
74. Pregosin P.S., Salzmann R. Coord. Chem. Rev. 155:1996;35.
75. Breutel C., Pregosin P.S., Salzmann R., Togni A. J. Am. Chem. Soc. 116:1994;4067.
76. Sprinz J., Kiefer M., Helmchen G., Reggelin M., Huttner G., Walter O., Zsolnai L. Tetrahedron Lett. 35:1994;1253.
77. Vrieze K., Cosee P., Praat A.P., Hilbers C.W. J. Organomet. Chem. 11:1968;353.
78. Wilke G. Angew. Chem. Int. Ed. Engl. 27:1988;186.
79. W. Keim, D. Vogt, R. Bayersdoerfer, DE 19,512,881, August 29, 1996; Chem. Abstr., 125, 248773t.
80. Bayersdörder R., Ganter B., Englert U., Keim W., Vogt D. J. Organomet. Chem. 552:1998;187.
81. S. Hattori, H. Munakata, K. Tatsuoka, T. Shimizu, US Patent 30,803,254, 1974; Chem. Abstr., 82, 44004b, 1975.
82. S. Hattori, H. Munakata, K. Tatsuoka, T. Shimizu, US Patent 30,803,254, 1974; Chem. Abstr., 82, 44004b, 1975.
83. E. Drent, US patent 5,227,561, 1993;
84. E. Drent, US patent 5,227,561, 1993; Chem. Abstr. 129, 31520v, 1994.
85. Britovsek, Keim G.P.W., Mecking S., Sainz D., Wagner T. J. Chem. Soc. Chem. Commun. 1993;1632.
86. Girolami G.S., Rauchfuss T.B., Angelici R.T. Synthesis and Techniques in Inorganic Chemistry: a Laboratory Manual. 1999;University Science Books, Sausalito.
87. Allen T.H., Kenard O. Chem. Design Automat. News. 8:1993;146.
88. Umakoski K., Kinoshita I., Ooi S. Inorg. Chim. Acta. 127:1987;L41.
89. Umakoski K., Ichimura A., Inoshita K., Ooi S. Inorg. Chem. 29:1990;4005.
90. Kubiak M. Acta Crystallogr. C. 41:1985;1288.
91. Deeming A.J., Meah M.N., Bates P.A., Hursthouse M.B. J. Chem. Soc. Dalton Trans. 1988;2193.
92. Padilla E.M., Yamamoto J.H., Jensen C.M. Inorg. Chim. Acta. 174:1990;209.
93. Caires A.C.F., Mauro A.E., de A. Santos R.H., Gambardella M.T.P., Lechat J.R. Gazz. Chim. Ital. 123:1993;495.
94. Yap G.P.A., Jensen C.M. Inorg. Chem. 31:1992;4823.
95. Engeslking M., Kerentzopoulos S., Reussmann G., Kebs B. Chem. Ber. 127:1994;2355.
96. Gupta M., Cramer R.E., Ho K., Pettersen C., Mishina S., Belli J., Jensen C.M. Inorg. Chem. 34:1995;60.
97. Tzeng B.C., Fu W.F., Che C.M., Chao H.Y., Cheung K.K., Peng S.M. J. Chem. Soc. Dalton Trans. 1999;1017.
98. Deeming A.J., Meah M.N., Bates P.A., Hursthouse M.B. J. Chem. Soc. Dalton Trans. 1988;235.
99. Fernández-Galan R., Manzano B.R., Otero A., Poujaud N., Kubicki M. J. Organomet. Chem. 579:1999;321.
100. Labelling of the atoms correspond to those shown in the schemes.
101. Labelling of the atoms correspond to those shown in Fig. 1.
102. 2- moiety is masked partially by the groups of signals observed in the range 3.80-4.10 ppm.