A trifunctional catalyst for one-pot synthesis of chiral diols via heck coupling-N-oxidation-asymmetric dihydroxylation: Application for the synthesis of diltiazem and taxol side chain

Journal of Organic Chemistry

Volumn 68, Issue 5, 2003, Pages 1736-1746

  Choudary, Boyapati M ^a   Chowdari, Naidu S ^a   Madhi, Sateesh ^a   Kantam, Mannepalli L ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

TRIFUNCTIONAL CATALYSTS;

ALCOHOLS; CATALYST ACTIVITY; ESTERS; HYDROXYLATION; OXYGEN; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS; X RAY PHOTOELECTRON SPECTROSCOPY;

CATALYSTS;

ALKENE; DILTIAZEM; MORPHOLINE DERIVATIVE; OSMIUM; PALLADIUM; TUNGSTEN;

ARTICLE; ARYLATION; BINDING AFFINITY; BINDING KINETICS; CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; CRYSTALLIZATION; DIHYDROXYLATION; DRUG SYNTHESIS; ENERGY; FOURIER TRANSFORMATION; GEOMETRY; INFRARED SPECTROSCOPY; ION EXCHANGE; OXIDATION; REACTION ANALYSIS; X RAY DIFFRACTION; X RAY PHOTOELECTRON SPECTROSCOPY;

CATALYSIS; DILTIAZEM; HYDROGEN PEROXIDE; MOLECULAR STRUCTURE; OSMIUM; OXIDATION-REDUCTION; OXIDES; PACLITAXEL; PALLADIUM; SPECTROMETRY, X-RAY EMISSION; TUNGSTEN;

EID: 0037424409     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026687i     Document Type: Article

References (104)

1. (a) Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry; Vogtle, F., Stoddart, J. F., Shibasaki, M., Eds.; Wiley-VCH: Weinheim, 2000; p 39.
2. (b) Hall, N. Science 1994, 266, 32.
3. (a) Domling, A.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1993, 32, 563.
4. (b) Roessner, C. A.; Scott, A. I. Chem. Biol. 1996, 3, 325.
5. (c) Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 766.
6. Yamasaki, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 1256.
7. For bifunctional catalysts, see: (a) Yu, H.-B.; Hu, Q.-S.; Pu, L. J. Am. Chem. Soc. 2000, 122, 6500.
8. (b) Shibasaki, M. Chemtracts: Org. Chem. 1999, 12, 979.
9. (c) Rowlands, G. J. Tetrahedron 2001, 57, 1865.
10. (d) France, S.; Wack, H.; Hafez, A. M.; Taggi, A. E.; Witsil, D. R.; Lectka, T. Org. Lett. 2002, 4, 1603.
11. (e) Groger, H. Chem. Eur. J. 2001, 7, 5247.
12. (f) Hamashima, Y.; Sawada, D.; Nogami, H.; Kanai, M.; Shibasaki, M. Tetrahedron 2001, 57, 805.
13. (a) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
14. (b) Marko, I. E.; Svendsen, J. S. In Comprehensive Asymmetric Catalysis II; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; p 723.
15. (c) Dobler, C.; Mehltretter, G.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 3026.
16. (d) Wai, J. S. M.; Marko, I. E.; Svendsen, J. S.; Finn, M. G.; Jacobsen, E. N.; Sharpless, K. B. J. Am. Chem. Soc. 1989, 111, 1123.
17. (a) Bolm, C.; Gerlach, A. Eur. J. Org. Chem. 1998, 21.
18. (b) Salvadori, P.; Pini, D.; Petri, A. Synlett 1999, 1181.
19. (c) Gravert, D. J.; Janda, K. D. Chem. Rev. 1997, 97, 489.
20. (d) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
21. (a) VanRheenen, V.; Kelly, R. C.; Cha, D. F. Tetrahedron Lett. 1976, 17, 1973.
22. (b) Kolb, H. C.; Sharpless, K. B. J. Org. Chem. 1994, 59, 5104.
23. (c) Wang, Z.-M.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302.
24. (d) Ahrgren, L.; Sutin, L. Org. Process Res. Dev. 1997, 1, 425.
25. (e) Lu, X.; Xu, Z.; Yang, G.; Org. Process Res. Dev. 2000, 4, 575.
26. (a) Singh, M. P.; Singh, H. S.; Arya, A. K.; Singh, A. K.; Sisodia, A. K. Indian J. Chem. 1975, 13, 112.
27. (b) Minata, M.; Yamamoto, K.; Tsuji, J. J. Org. Chem. 1990, 55, 766.
28. (c) Sharpless, K. B.; Amberg, W.; Beller, M.; Chen, H.; Hartung, J.; Kawanami, Y.; Lubben, D.; Manoury, E.; Ogino, Y.; Shibata, T.; Ukita, T. J. Org. Chem. 1991, 56, 4585.
29. (d) Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448.
30. (a) Krief, A.; Colaux-Castillo, C. Tetrahedron Lett. 1999, 40, 4189.
31. (b) Dobler, C.; Mehltretter, G.; Sundermeier, U.; Beller, M. J. Am. Chem. Soc. 2000, 122, 10289.
32. (c) Dobler, C.; Mehltretter, G.; Sundermeier, U.; Beller, M. J. Organomet. Chem. 2001, 621, 70.
33. Milas, N. A.; Sussman, S. J. Am. Chem. Soc. 1936, 58, 1302.
34. (a) Bergstad, K.; Jonsson, S. Y.; Bäckvall, J.-E. J. Am. Chem. Soc. 1999, 121, 10424.
35. (b) Jonsson, S. Y.; Farnegardh, K.; Bäckvall, J.-E. J. Am. Chem. Soc. 2001, 123, 1365.
36. (c) Jonsson, S. Y.; Adolfsson, H.; Bäckvall, J.-E. Org. Lett. 2001, 3, 3465.
37. (d) Ell, A. H.; Jonsson, S. Y.; Borje, A.; Adolfson, H.; Bäckvall, J.-E. Tetrahedron Lett. 2001, 42, 2569.
38. (a) Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094.
39. (b) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
40. (c) Kobayashi, S.; Ishida, T.; Akiyama, R. Org. Lett. 2001, 3, 2649.
41. (a) Choudary, B. M.; Chowdari, N. S.; Madhi, S.; Kantam, M. L. Angew. Chem., Int. Ed. 2001, 40, 4620.
42. (b) Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Kantam, M. L. J. Am. Chem. Soc. 2002, 124, 5341.
43. (c) Choudary, B. M.; Chowdari, N. S.; Kantam, M. L.; Raghavan, K. V. J. Am. Chem. Soc. 2001, 123, 9220.
44. Severeyns, A.; De Vos, D. E.; Fiermans, L.; Verpoort, F.; Grobet, P. J.; Jacobs, P. A. Angew. Chem., Int. Ed. 2001, 40, 586.
45. We have also tested Ti(IV) as an ETM, and the results are inferior; see: Choudary, B. M.; Chowdari, N. S.; Jyothi, K.; Madhi, S.; Kantam, M. L. Adv. Synth. Catal. 2002, 344, 503.
46. For LDH, see: (a) Choudary, B. M.; Kantam, M. L.; Kavita, B.; Reddy, C. V.; Rao, K. K.; Figueras, F. Tetrahedron Lett. 1998, 39, 3555.
47. (b) Sels, B.; De Vos, D.; Buntinx, M.; Pierard, F.; Kirsch-De Mesmaeker, A.; Jacobs, P. A. Nature 1999, 400, 855.
48. (c) Choudary, B. M.; Bharathi, B.; Reddy, C. V.; Kantam, M. L.; Raghavan, K. V. Chem. Commun. 2001, 1736.
49. (d) Sels, B.; De Vos, D.; Jacobs, P. A. J. Am. Chem. Soc. 2001, 123, 8350.
50. (e) Choudary, B. M.; Kantam, M. L.; Rahman, A.; Reddy, C. V.; Rao, K. K. Angew. Chem., Int. Ed. 2001, 40, 763.
51. (f) Kantam, M. L.; Choudary, B. M.; Reddy, C. V.; Rao, K. K.; Figueras, F. Chem. Commun. 1998, 763.
52. (g) Rao, K. K.; Gravelle, M.; Sanchez, J.; Figueras, F. J. Catal. 1998, 173, 115.
53. (h) Corma, A.; Martin-Aranda, R. M. J. Catal. 1991, 130, 130.
54. Modified silica: (a) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907.
55. (b) Hoegaerts, D.; Sels, B. F.; De Vos, D. E.; Verpoort, F.; Jacobs, P. A. Catal. Today 2000, 60, 209.
56. Resins: (a) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
57. (b) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977.
58. (c) Roscoe, S. B.; Frechet, J. M.; Walzer, J. F.; Dias, A. J. Science 1998, 280, 270.
59. (a) Trifiro, F.; Vaccari, A. Comprehensive Supramolecular Chemistry; Pergamon: Elsevier Science: Oxford, 1996; Vol. 7, p 251.
60. (b) Miyata, S. Clays Clay Miner. 1975, 23, 369.
61. (a) Miyata, S. Clays Clay Miner. 1983, 31, 305.
62. (b) Dutta, P. K.; Puri, M. J. Phys. Chem. 1989, 93, 367.
63. (c) Parker, L. M.; Milestone, N. B.; Newman, R. H. Ind. Eng. Chem. Res. 1995, 34, 1196.
64. (d) Hibino, T.; Tsunashima, A. Chem. Mater. 1998, 10, 4055.
65. (e) Takagi, K.; Shichi, T.; Usami, H.; Sawaki, Y. J. Am. Chem. Soc. 1993, 115, 4339.
66. (f) Yao, K.; Taniguchi, M.; Nakata, M.; Takahashi, M.; Yamagishi, A. Langmuir 1998, 14, 2890.
67. Choy, J. H.; Kwak, S. Y.; Park, S. J.; Jeong, Y. J.; Porier, J. J. Am. Chem. Soc. 1999, 121, 1399.
68. ESCA of Os: (a) White, D. L.; Andrews, S. B.; Faller, J. W.; Barrnett, R. J. Biochim. Biophys. Acta 1976, 436, 577.
69. (b) Burroughs, P.; Evans, S.; Hamnett, A.; Orchard, A. F.; Richardson, N. V. J. Chem. Soc., Faraday Trans. 1974, 12, 1895.
70. (c) Moulder, J. F.; Stickle, W. F.; Sobol, P. E.; Bomden, K. D. Handbook of X-ray Photoelectron Spectroscopy; Perkin-Elmer Corp.: Minneapolis, MN, 1992.
71. ESCA of W: (a) Sohn, J. R.; Park, M. Y. Langmuir 1998, 14, 6140.
72. (b) Dong, L.; Hu, Y.; Xu, F.; Lu, D.; Xu, B.; Hu, Z.; Chen, Y. J. Phys. Chem. B 2000, 104, 78.
73. (c) Peng, Y.; Meng, Z.; Zhong, C.; Lu, J.; Yang, Z.; Qian, Y. Chem. Lett. 2001, 64.
74. ESCA of Pd: (a) Kumar, G.; Blackburn, J. R.; Albridge, R. G.; Moddeman, W. E.; Jones, M. M. Inorg. Chem. 1972, 11, 296.
75. (b) Kili, K.; Hilaire, L.; Normand, F. L. Phys. Chem. Chem. Phys. 1999, 1, 1623.
76. (c) Verduraz, F. B.; Omar, A.; Escard, J.; Pontvianne, B. J. Catal. 1978, 53, 126.
77. Donohoe, T. J.; Waring, M. J.; Newcombe, N. J. Synlett 2000, 1, 149.
78. Dupau, P.; Epple, R.; Thomas, A. A.; Fokin, V. V.; Sharpless, K. B. Adv. Synth. Catal. 2002, 344, 421.
79. AD of trisubstituted olefins: (a) Rosini, C.; Scamuzzi, S.; Focati, M. P.; Salvadori, P. J. Org. Chem. 1995, 60, 8289.
80. (b) Mehltretter, G. M.; Dobler, C.; Sundermeier, U.; Beller, M. Tetrahedron Lett. 2000, 41, 8083.
81. (c) Battaglia, A.; Barbaro, G.; Giorgianni, P.; Guerrinni, A.; Bertucci, C.; Geremia, S. Chem. Eur. J. 2000, 6, 3551.
82. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
83. Nagao, T.; Sato, M.; Nakajima, H.; Kiyomoto, A. Chem. Pharm. Bull. 1973, 21, 92.
84. (a) Watson, K. G.; Fung, Y. M.; Gredley, M.; Bird, G. J.; Jackson, W. R.; Gountzos, H.; Matthews, B. R. Chem. Commun. 1990, 1018.
85. (b) Yamamoto, M.; Hayashi, M.; Masaki, M.; Nohira, H. Tetrahedron: Asymmetry 1991, 2, 403.
86. (c) Schwartz, A.; Madan, P. B.; Mohacsi, E.; O'Brien, J. P.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1992, 57, 4320.
87. (d) Chang, S.; Galvin, J. M.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 6937.
88. (e) Lohray, B. B.; Jayachandran, B.; Bhushan, V.; Nandanan, E.; Ravidranathan, T. J. Org. Chem. 1995, 60, 5983.
89. (f) Imashiro, R.; Kuroda, T. Tetrahedron Lett. 2001, 42, 1313.
90. (g) Gentile, A.; Giordano, C.; Fuganti, C.; Ghirotto, L.; Servi, S. J. Org. Chem. 1992, 57, 6635.
91. Taxol side chain: (a) Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
92. (b) Nicolaou K. C. et al. Nature 1994, 367, 630.
93. Della Casa de Marcano, D. P.; Halsall, T. G. Chem. Commun. 1975, 365.
94. (a) Denis, J. N.; Greene, A. E.; Serra, A. A.; Luche, M. J. J. Org. Chem. 1986, 51, 46.
95. (b) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 1957.
96. (c) Ojima, I.; Habus, I.; Zhao, M.; Georg, G. I.; Jayasinghe L. R. J. Org. Chem. 1991, 56, 1681.
97. (d) Denis, J. N.; Correa, A.; Greene, A. E. J. Org. Chem. 1990, 55, 6939.
98. (e) Honig, H.; Seufer-Wasserthal, P.; Weber, H. Tetrahedron 1990, 46, 3841.
99. (f) Deng, L.; Jacobsen, E. N. J. Org. Chem. 1992, 57, 4320.
100. (a) Fleming, P. R.; Sharpless, K. B. J. Org. Chem. 1994, 59, 8302.
101. (b) Lee, D.; Kim, M.-J. Tetrahedron Lett. 1998, 39, 2163.
102. Cainelli, G.; Contento, M.; Manescalchi, F.; Plessi, L. Synthesis 1989, 45.
103. Choudary, B. M.; Sateesh, M.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
104. Matsuura, F.; Hamada, Y.; Shioiri, T. Tetrahedron 1994, 50, 9457.