Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins

Journal of Organic Chemistry

Volumn 62, Issue 11, 1997, Pages 3575-3581

  Yu, Libing ^a   Chen, Depu ^a   Li, Jun ^a   Wang, Peng George ^a  

^a Department of Biology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001001230     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961933+     Document Type: Article

References (91)

1. (a) Merrifield, R. B. Angew. Chem., Int. Ed. Engl. 1985, 24, 799.
2. (b) Barany, G.; Kneib-Cordonier, N.; Mullen, D. G. Int. J. Pept. Protein Res. 1987, 30, 705.
3. (c) Kent, S. B. H. Annu. Rev. Biochem. 1988, 57, 957.
4. (a) Letsinger, R. L.; Mahadevan, V. J. Am. Chem. Soc. 1965, 87, 3526.
5. (b) Sproat, B. S.; Gait, M. J. Oligonucleotide Synthesis: a Pratical Approach; IRL Press: Oxford, 1984; p 83.
6. (b) Atkinson, T.; Smith, M. In Oligonucleotide Synthesis: a Practical Approach; Gait, M. J., Ed.; IRL Press: Oxford, 1984; p 35.
7. (c) Froehler, B. C.; Ng, P. G.; Matteucci, M. D. Nucleic Acids Res. 1986, 14, 5399.
8. (d) Blackburn, G. M., Gait, M. J., Eds. Nucleic Acids in Chemistry and Biology; IRL Press: Oxford, 1990.
9. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
10. (b) Fruchtel, J. S.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 17.
11. (a) Strocker, A. M.; Keating, T. A.; Tempeat, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149.
12. (b) Dinh, T. Q.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1161.
13. Fetizon, M.; Golfier, M. C. R. Acad. Sci. Ser. 1968, C 267, 900.
14. Clark, J. H. Catalysis of Organic Reactions by Supported Inorganic Reagents; VCH: New York, 1994.
15. For a review book, see: Solid Supports and Catalysts in Organic Synthesis; Smith, K., Ed.; Ellis Harwood PTR Prentice Hall: New York, 1992.
16. (a) Sherrington, D. C., Hodge, P., Ed. Synthesis and Separations Using Functional Polymers; John Wiley & Sons: New York, 1988.
17. (b) Frechet, J. M.; Draling, G. D.; Itsuno, S.; Lu, P.-L.; Meftah, M. V.; Rolls, W. A., Jr. Pure Appl. Chem. 1988, 60, 353.
18. (c) Laszlo, P., Ed. Preparative Chemistry Using Supported Reagents; Academic Press: London, 1987.
19. (d) Ford, W. T., Ed. Polymeric Reagents and Catalysts; ACS Symp. Ser. 308; American Chemical Society: Washington, DC, 1986.
20. (e) Hodge, P., Sherrington, D. C., Eds. Polymer-Supported Reactions in Organic Synthesis; John Wiley & Sons: New York, 1980.
21. For applications of lanthanides in organic synthesis, see reviews and a book: Molander, G. Chem. Rev. 1992, 92, 29. (b) Marshman, R. Aldrichim. Acta 1995, 28, 77. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
22. For applications of lanthanides in organic synthesis, see reviews and a book: Molander, G. Chem. Rev. 1992, 92, 29. (b) Marshman, R. Aldrichim. Acta 1995, 28, 77. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
23. For applications of lanthanides in organic synthesis, see reviews and a book: Molander, G. Chem. Rev. 1992, 92, 29. (b) Marshman, R. Aldrichim. Acta 1995, 28, 77. (c) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994.
24. (a) Ho, T.-L. Synthesis 1973, 347.
25. (b) Ho, T.-L. Organic Synthesis by Oxidation with Metal Compounds; Mijs, W. J., de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1977; p 330.
26. Kanemoto, S.; Saimoto, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 3317.
27. (a) Luche, J.-L. J. Am. Chem. Soc, 1978, 100, 2226.
28. (b) Luche, J.-L.; Rodriguez-Hahn, L.; Crabbe, P. J. Chem. Soc., Chem. Commun. 1978, 601.
29. (c) Gemal, A. L.; Luche, J.-L. J. Am. Chem. Soc. 1981, 103, 545
30. (a) Soderquist, J. A. Aldrichim. Acta 1991, 24, 15.
31. (b) Molander, G. Org. React. 1994, 46, 211.
32. (a) Yu, L.-B.; Chen, D.-P.; Wang, P. Tetrahedron Lett. 1996, 37, 2169.
33. (b) Chen, D.-P.; Yu, L.-B.; Wang, P. Tetrahedron Lett. 1996, 37, 4467.
34. (c) Yu, L.-B.; Chen, D.-P.; Li, J.; Wang, P.; Bott., S. J. Org. Chem. 1997, 62, 208.
35. (d) Yu, L.-B.; Li, J.; Ramirez, J.; Chen, D.-P.; Wang, P. G. J. Org. Chem. 1997, 62, 907.
36. (a) Strelow, F. W. E.; Rethemeyer, R.; Bothma, C. J. C. Anal. Chem. 1965, 37, 106.
37. (b) Strelow, F. W. E.; Van Zyl, C. R.; Bothma, C. J. C. Anal. Chim. Acta 1969, 45, 81.
38. (a) Kabashayi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
39. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977.
40. (a) Remers, W. Chem. Heterocycl. Compd. 1972, 25 -(1), 1.
41. (b) Jones, R.; Bean, G. The Chemistry of Pyrroles; Academic Press: London, 1977.
42. (a) Gregorovich, B.; Liang, K.; Clugston, D.; MacDonald, S. Can. J. Chem. 1968, 46, 3291.
43. (b) Roomi, M.; MacDonald, S. Can. J. Chem. 1970, 48, 139.
44. (a) Chatterjee, A.; Manna, S.; Benerji, J.; Pascard, C.; Prange, T.; Shoolery, J. J. Chem. Soc., Perkin Trans. I 1980, 553.
45. (b) Banerji, J.; Chatterjee, A.; Manna, S.; Pascard, C.; Prange, T.; Shoolery, J. Heterocycles 1981, 15, 325.
46. (c) Roder, E. Arch. Pharm. (Weinheim, Ger.) 1972, 305, 96.
47. (d) Roder, E. Arch. Pharm. (Weinheim, Ger.) 1972, 305, 117.
48. (e) Noland, W.; Venkiteswaren, M.; Richards, C. J. Org. Chem. 1961, 26, 4241.
49. (a) Vougioukas, A. E.; Kagan, H. B. Tetrahedron Lett. 1987, 28, 5513.
50. (b) Kobayashi, S. Synthesis 1993, 371.
51. Luche, J.-L.; Gemal, A. L. J. Chem. Soc., Chem. Commun. 1978, 976.
52. Mori, S.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1986, 27, 6111.
53. (a) Taylor, M. D.; Minaskanian, G.; Winzenberg, K. N.; Santone, P.; Smith, A. B., III. J. Org. Chem. 1982, 47, 3960.
54. (b) Satoh, T.; Kaneko, Y.; Okuda, T.; Uwaya, S.; Yamakawa, K. Chem. Pharm. Bull. 1984, 32, 3452.
55. (c) Cockerill, G. S.; Kocienski, P.; Treadgold, R. J. Chem. Soc., Perkin Trans. 1 1985, 2101.
56. (d) Arai, Y.; Yamamoto, M.; Koizumi, T. Bull. Chem. Soc. Jpn. 1988, 61, 467.
57. (e) Kuo, D. L.; Money, T. Can. J. Chem. 1988, 66, 1794.
58. (f) Brandes, E.; Grieco, P. A.; Garner, P. J. Chem. Soc., Chem. Commun. 1988, 500.
59. (g) Baudouy, R.; Prince, P. Tetrahedron 1989, 45, 2067.
60. (a) Mukaiyama, T.; Narasaka, K.; Banno, T. Chem. Lett. 1973, 1101.
61. (b) Mukaiyama, T.; Narasaka, K.; Banno, T. J. Am. Chem. Soc. 1974, 96, 7503.
62. (a) Kobayashi, S. Chem. Lett. 1991, 2087.
63. (b) Kabayashi, S.; Hachiya, I. J. Org. Chem. 1994, 3590.
64. (c) Kobayashi, S.; Hachiya, I. Tetrahedron Lett. 1992, 33, 1625.
65. Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. Synlett 1995, 233.
66. (a) Hachiya, I.; Kobayashi, S. J. Org. Chem. 1993, 58, 6958.
67. (b) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
68. (a) Larsen, S. D.; Grieco, P. A. J. Am. Chem. Soc. 1985, 107, 1768-1769.
69. (b) Grieco, P. A.; Larsen, S. D.; Fobare, W. F. Tetrahedron Lett. 1986, 27, 1975-1978.
70. (c) Grieco, P. A.; Parker, D. T.; Fobare, W. F.; Ruckle, R. J. Am. Chem. Soc. 1987, 109, 5859-5861.
71. (d) Grieco, P. A.; Bahsas, A. J. Org. Chem. 1987, 52, 5746-5749.
72. (e) Grieco, P. A.; Clark, J. D. J. Org. Chem. 1990, 55, 2271-2272.
73. (f) Grieco, P. A.; Larsen, S. D. Org. Synth. 1990, 68, 206-209.
74. (a) Waldmann, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 274-275.
75. (b) Waldmann, H. Liebigs Ann. Chem. 1989, 231-238.
76. (c) Walma, H.; Braun, M. Liebigs Ann. Chem. 1991, 1045-1048.
77. (d) Bailey, P. D.; Brown, G. R.; Korber, F.; Reed, A.; Wilson, R. D. Tetrahedron: Asymmetry 1991, 2, 1263-1282.
78. (e) Bailey, P. D.; Wilson, R. D.; Brown, G. R. J. Chem. Soc., Perkin Trans. I 1991, 1337-1340.
79. (f) Stella, L.; Abraham, H.; Feneau-Dupont, J.; Tinant, B.; Decercq, J. P. Tetrahedron Lett. 1990, 31, 2603-2606.
80. (g) Abraham, H.; Stella, L. Tetrahedron 1992, 48, 9707-9718.
81. (a) Moguro, M.; Asao, N.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1994, 2597.
82. (b) Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
83. Matsubara, S.; Onishi, H.; Utimoto, K. Tetrahedron Lett. 1990, 31, 6209.
84. (a) Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
85. (b) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503 and references cited therein.
86. (a) Hosono, S.; Kim, W.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 4-5.
87. (b) Kim, W.; Hosono, S.; Sasai, H.; Shibasaki, M. Tetrahedron Lett. 1995, 36, 25, 4443.
88. (c) Kim, W.; Hosono, S.; Sasai, H.; Shibasaki, M. Heterocydes 1996, 42, 795-809.
89. Davis, T. S.; Gattys, G. A.; Kubler, D. G. J. Org. Chem. 1976, 41, 2349.
90. Stoll, M.; Bottle, P. Helv. Chim. Acta 1948, 31, 4.
91. Jansson, P.-E.; Kenne, L.; Schweda, E. J. Chem. Soc., Perkin Trans. I 1987, 377.