Cationic [2,6-Bis(2′-oxazolinyl)phenyl]palladium(II) Complexes: Catalysts for the Asymmetric Michael Reaction

Organometallics

Volumn 19, Issue 7, 2000, Pages 1282-1291

  Stark, Mark A ^a   Jones, Geraint ^a   Richards, Christopher J ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001060597     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990710h     Document Type: Article

References (91)

1. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020.
2. (a) Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6.
3. (b) Nemeh, S.; Jensen, C.; Binamira-Soriaga, E.; Kaska, W. C. Organometallics 1983, 2, 1442.
4. (c) Haenel, M. W.; Jakubik, D.; Krüger, C.; Betz, P. Chem. Ber. 1991, 124, 333.
5. Bennett, M. A.; Jin, H.; Willis, A. C. J. Organomet. Chem. 1993, 451, 249.
6. (e) Steffey, B. D.; Miedaner, A.; Maciejewski-Farmer, M. L.; Bernatis, P. R.; Herring, A. M.; Allured, V. S.; Carperos, V.; DuBois, D. L. Organometallics 1994, 13, 4844.
7. (f) Cross, R. J.; Kennedy, A. R.; Muir, K. W. J. Organomet. Chem. 1995, 487, 227.
8. (g) Cross, R. J.; Kennedy, A. R.; Manojlovic-Muir, L.; Muir, K. W. J. Organomet. Chem. 1995, 493, 243.
9. (h) Karlen, T.; Dani, P.; Grove, D. M.; Steenwinkel, P.; van Koten, G. Organometallics 1996, 15, 5687.
10. Jia, G.; Lee, H. M.; Williams, I. D. J. Organomet. Chem. 1997, 534, 173.
11. (j) Dani, P.; Karlen, T.; Gossage, R. A.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1997, 119, 11317.
12. (k) Vigalok, A.; Uzan, O.; Shimon, L. J. W.; BenDavid, Y.; Martin, J. M. L.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 12539.
13. (a) Errington, J.; McDonald, W. S.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1980, 2312.
14. (b) Kickham, J. E.; Loeb, S. J. Inorg. Chem. 1994, 33, 4351.
15. (c) Kickham, J. E.; Loeb, S. J. Organometallics 1995, 14, 3584.
16. Kickham, J. E.; Loeb, S. J.; Murphy, S. L. Chem. Eur. J. 1997, 3, 1203.
17. (a) Mehring, M.; Schümann, M.; Jurkschat, K. Organometallics 1998, 17, 1227.
18. (b) Vicente, J.; Arcas, A.; Blasco, M.-A.; Lozano, J.; de Arellano, M. C. R. Organometallics 1998, 17, 5374.
19. (a) Grove, D. M.; van Koten, G.; Ubbels, H. J. C.; Spek, A. L. J. Am. Chem. Soc. 1982, 104, 4285.
20. (b) Grove, D. M.; van Koten, G.; Louwen, J. N.; Noltes, J. G.; Spek, A. L.; Ubbels, H. J. C. J. Am. Chem. Soc. 1982, 104, 6609.
21. (c) Grove, D. M.; van Koten, G.; Ubbels, H. J. C.; Zoet, R. Organometallics 1984, 3, 1003.
22. Terheijden, J.; van Koten, G.; Groves, D. M.; Vrieze, K.; Spek, A. L. J. Chem. Soc., Dalton Trans. 1987, 1359.
23. (e) Van Koten, G. Pure Appl. Chem. 1989, 61, 1681.
24. (f) Gossage, R. A.; Ryabov, A. D.; Spek, A. L.; Stufkens, D. J.; van Beek, J. A. M.; van Eldik, R.; van Koten, G. J. Am. Chem. Soc. 1999, 121, 2488 and references therein.
25. Gandelman, M.; Vigalok, A.; Shimon, L. J. W.; Milstein, D. Organometallics 1997, 16, 3981.
26. (a) Gozin, M.; Weisman, A.; Ben-David, Y.; Milstein, D. Nature 1993, 364, 699.
27. (b) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1995, 117, 9774.
28. (c) Liou, S.-Y.; Gozin, M.; Milstein, D. J. Chem. Soc., Chem. Commun. 1995, 1965.
29. Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406.
30. (e) van der Boom, M. E.; Kraatz, H.-B.; Ben-David, Y.; Milstein, D. Chem. Commun. 1996, 2167.
31. (f) Liou, S.-Y.; van der Boom, M. E.; Milstein, D. Chem. Commun. 1998, 687.
32. (g) van der Boom, M. E.; Liou, S.-Y.; Ben-David, Y.; Gozin, M.; Milstein, D. J. Am. Chem. Soc. 1998, 120, 13415.
33. (h) van der Boom, M. E.; Higgitt, C. L.; Milstein, D. Organometallics 1999, 18, 2413.
34. (a) Gupta, M.; Hagen, C.; Flesher, R. J.; Kaska, W. C.; Jensen, C. M. Chem. Commun. 1996, 2083.
35. (b) Gupta, M.; Kaska, W. C.; Jensen, C. M. Chem. Commun. 1997, 461.
36. (c) Xu, W. W.; Rosini, G. P.; Gupta, M.; Jensen, C. M.; Kaska, W. C.; Krogh-Jespersen, K.; Goldman, A. S. Chem. Commun. 1997, 2273.
37. Gupta, M.; Hagen, C.; Kaska, W. C.; Cramer, R. E.; Jensen, C. M. J. Am. Chem. Soc. 1997, 119, 840.
38. (e) Lee, D. W.; Kaska, W. C.; Jensen, C. M. Organometallics 1998, 17, 1.
39. (a) Grove, D. M.; van Koten, G.; Verschuuren, A. H. M. J. Mol. Catal. 1988, 45, 16 9.
40. (b) Grove, D. M.; Verschuuren, A. H. M.; van Koten, G.; van Beek, J. A. M. J. Organomet. Chem. 1989, 372, C1.
41. (c) Knapen, J. W. J.; van der Made, A. W.; de Wilde, J. C.; van Leeuwan, P. W. N. M.; Wijkens, P.; Grove, D. M.; van Koten, G. Nature 1994, 372, 659.
42. van de Kuil, L. A.; Grove, D. M.; Gossage, R. A.; Zwikker, J. W.; Jenneskens, L. W.; Drenth, W.; van Koten, G. Organometallics 1997, 16, 4985.
43. (e) Gossage, R. A.; van de Kuil, L. A.; van Koten, G. Acc. Chem. Res. 1998, 31, 423.
44. Ohff, M.; Ohff, A.; van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687.
45. (a) Gorla, F.; Venanzi, L. M. Organometallics 1994, 13, 43.
46. (b) Gorla, F.; Togni, A.; Venanzi, L. M.; Albinati, A.; Lianza, F. Organometallics 1994, 13, 1607.
47. (c) Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1997, 38, 1725.
48. Longmire, J. M.; Zhang, X.; Shang, M. Organometallics 1998, 17, 4374.
49. (a) van de Kuil, L. A.; Veldhuizen, Y. S. J.; Grove, D. M.; Zwikker, J. W.; Jenneskens, L. W.; Drenth, W.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. Recl. Trav. Chim. Pays-Bas 1994, 113, 267.
50. (b) See also: Donkervoot, J. G.; Vicario, J. L.; Jastrzebski, J. T. B. H.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Organomet. Chem. 1998, 551, 1.
51. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K. Organometallics 1991, 10, 500.
52. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S.-B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223.
53. Nesper, R.; Pregosin, P.; Püntener, K.; Wörle, M.; Albinati, A. J Organomet. Chem. 1996, 507, 85.
54. (a) Gupta, A. D.; Bhuniya, D.; Singh, V. K. Tetrahedron 1994, 50, 13725.
55. (b) Evans, D. A.; Murry, J. A.; von Matt, P.; Norcross, R. D.; Miller, S. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 798.
56. (c) Gupta, A. D.; Singh, V. K. Tetrahedron Lett. 1996, 37, 2633.
57. Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
58. (e) Evans, D. A.; Kozlowski, M. C.; Tedrow, J. S. Tetrahedron Lett. 1996, 37, 7481.
59. Preliminary communications: (a) Stark, M. A.; Richards, C. J. Tetrahedron Lett. 1997, 38, 5881. (b) Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, MA, 1998; American Chemical Society: Washington, DC, 1998; ORGN 540.
60. Preliminary communications: (a) Stark, M. A.; Richards, C. J. Tetrahedron Lett. 1997, 38, 5881. (b) Abstracts of Papers, 216th National Meeting of the American Chemical Society, Boston, MA, 1998; American Chemical Society: Washington, DC, 1998; ORGN 540.
61. Denmark, S. E.; Stavenger, R. A.; Faucher, A. M.; Edwards, J. P. J. Org. Chem. 1997, 62, 3375.
62. Motoyama, Y.; Makihara, N.; Mikami, Y.; Aoki, K.; Nishiyama, H. Chem. Lett. 1997, 951.
63. Motoyama, Y.; Mikami, Y.; Kawakami, H.; Aoki, K.; Nishiyama, H. Organometallics 1999, 18, 3584.
64. Motoyama, Y.; Narusawa, H.; Nishiyama, H. Chem. Commun. 1999, 131.
65. Harris, T. D.; Neuschwander, B.; Boekelheide, V. J. Org. Chem. 1978, 43, 727.
66. Bolm, C.; Weickhardt, K.; Zehnder, M.; Ranff, T. Chem. Ber. 1991, 124, 1173.
67. (a) Newkome, G. R.; Puckett, W. E.; Gupta, V. K.; Kiefer, G. E. Chem. Rev. 1986, 86, 451.
68. (b) Ryabov, A. D.; Chem. Rev. 1990, 90, 403.
69. Izumi, T.; Watabe, H.; Kasahara, A. Bull. Chem. Soc. Jpn. 1981, 54, 1711.
70. Vorbrüggen, H.; Krolikliewicz, K. Tetrahedron Lett. 1981, 22, 4471.
71. During the course of this work we also synthesized (S,S)-1,3-bis[4′-(cyclohexylmethyl)-5′,5′-dimethyl-2′- oxazolinyl]benzene but were unable to effect the lithiation and/or palladation of this material. Full details on the synthesis of this and related oxazolines will be reported elsewhere.
72. (a) Patterman, S. P.; Karle, I. L.; Stucky, G. D. J. Am. Chem. Soc. 1970, 92, 1150.
73. (b) Rhine, W. E.; Stucky, G. D. J. Am. Chem. Soc. 1975, 97, 737.
74. Strauss, S. H. Chem. Rev. 1993, 93, 927.
75. Olgemöller, B.; Olgemöller, L.; Beck, W. Chem. Ber. 1981, 114, 2971.
76. Hayashi, T.; Sawamura, M.; Ito, Y. Tetrahedron 1992, 48, 1999.
77. (a) Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S.-I. J. Am. Chem. Soc. 1989, 111, 5954.
78. (b) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaya, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hiranao, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
79. Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1991, 32, 2807.
80. (a) Sawamura, M.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295.
81. (b) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
82. (c) Sawamura, M.; Hamashima, H.; Shinoto, H.; Ito, Y. Tetrahedron Lett. 1995, 36, 6479.
83. Sawamura, M.; Sudoh, M.; Ito, Y. J. Am. Chem. Soc. 1996, 118, 3309.
84. (e) Inagaki, K.; Nozaki, K.; Takaya, H. Synlett 1997, 119.
85. (f) Kuwano, R.; Miyazaki, H.; Ito, Y. Chem. Commun. 1998, 71.
86. (g) Blacker, A. J.; Clarke, M. L.; Loft, M. S.; Mahon, M. F.; Williams, J. M. J. Organometallics 1999, 18, 2867.
87. (a) Mizuho, Y.; Kasuga, N.; Komiya, S. Chem. Lett. 1991, 2127.
88. (b) Hirano, M.; Takenaka, A.; Mizuho, Y.; Hiraoka, M.; Komiya, S. J. Chem. Soc., Dalton Trans. 1999, 3209.
89. Sammakia, T.; Latham, H. A.; Schaad, D. R. J. Org. Chem. 1995, 60, 10.
90. Broadhead, G. D.; Osgerby, J. M.; Pauson, P. L. Chem. Ind. 1957, 209
91. Locke, A. J.; Richards, C. J. Organometallics 1999, 18, 3750.