Toward truly efficient organic reactions in water

Process Chemistry in the Pharmaceutical Industry, Volume 2: Challenges in an Ever Changing Climate

Volumn , Issue , 2007, Pages 249-265

  Ogawa, Chikako ^a   Kobayashi, Shū ^b  

^a EISAI RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79955758074     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420008357     Document Type: Chapter

References (92)

1. Li, C.-J. and Chan, T.-H. Organic Reactions in Aqueous Media, Wiley & Sons, New York, 1997.
2. Grieco, P.A., Ed., Organic Synthesis in Water, Blackie Academic and Professional: London, 1998.
3. Lindstroem, U.M. Chem. Rev., 2002, 102, 2751.
4. Sinou, D. Adv. Synth. Catal., 2002, 344, 237.
5. Li, C-J. Chem. Rev., 2005, 105, 3095.
6. Schinzer, D., Ed., Selectivities in Lewis Acid Promoted Reactions, Kluwer Academic: Boston, 1989.
7. Yamamoto, H., Ed., Lewis Acids in Organic Synthesis, Wiley-VCH: New York, 2000.
8. Hay, R.W. Lewis acid catalysis and the reactions of coordinated ligands, in Comprehensive Coordination Chemistry, Wilkinson, G.R., Gillard, D., and McCleverty, J.A., Eds., Pergamon Press: Elmsford, NY, Vol. 6, p. 411.
9. Kobayashi, S. Lanthanide triflate-catalyzed carbon-carbon bond-forming reactions in organic synthesis, in Lanthanides: Chemistry and Use in Organic Synthesis, Kobayashi, S., Ed., Springer Publishing: New York, 1999, p. 63.
10. Kobayashi, S. Eur. J. Org. Chem., 1999, 15.
11. Kobayashi, S. Synlett, 1994, 689.
12. Kobayashi, S., Sugiura, M., Kitagawa, H., and Lam, W.W.-L. Chem. Rev., 2002, 102, 2227.
13. Kobayashi, S. Chem. Lett., 1991, 2187.
14. Kobayashi, S. and Hachiya, I. J. Org. Chem., 1994, 59, 3590.
15. Kobayashi, S., Nagayama, S., and Busujima, T. J. Am. Chem. Soc., 1998, 120, 8287.
16. Baes, C.F., Jr. and Mesmer, R.E. The Hydrolysis of Cations, Wiley & Sons: New York, 1976.
17. Yatsimirksii, K.B. and Vasil’ev, V.P. Instability Constants of Complex Compounds, Pergamon: New York, 1960.
18. Martell, A.E., Ed., Coordination Chemistry ACS Monograph 174, Vol. 2, American Chemical Society: Washington, DC, 1978.
19. Fringuelli, F., Pizzo, F., and Vaccaro, L. J. Org. Chem., 2001, 66, 3554.
20. Manabe, K., et al. J. Am. Chem. Soc., 2000, 122, 7202.
21. Kobayashi, S., Busujima, T., and Nagayama, S. J. Chem. Soc., Chem. Commun., 1998, 19.
22. Manabe, K. and Kobayashi, S. Chem. Commun. 2000, 669.
23. Mori, Y., Kakumoto, K., Manabe, K., and Kobayashi, S. Tetrahedron Lett., 2000, 41, 3107.
24. Manabe, K., Aoyama, N., and Kobayashi, S. Adv. Synth. Catal., 2001, 343, 174.
25. Manabe, K., Sun, X.-M., and Kobayashi, S. J. Am. Chem. Soc., 2001, 123, 10101.
26. Manabe, K., et al. J. Am. Chem. Soc., 2002, 124, 11971, and references therein.
27. Kobayashi, S., Iimura, S., and Manabe, K. Chem. Lett., 2002, 10.
28. Blatt, A.H. and Gross, N.J. Org. Chem. 1964, 29, 3306.
29. Yi, L., Zou, J., Lei, H., Lin, X., and Zhang, M. Org. Prep. Proceed. Int. 1991, 23, 673.
30. Manabe, K. and Kobayashi, S. Org. Lett., 1999, 1, 1965.
31. Cornils, B. and Herrmann, W.A., Eds. Aqueous-Phase Organometallic Catalysis, 2nd ed., Wiley-VCH: New York, 2004.
32. Manabe, K. and Kobayashi, S. Chem. Eur. J. 2002, 8, 4094.
33. Kobayashi, S., Nagayama, S., and Busujima, T. Chem. Lett., 1999, 71.
34. Nagayama, S. and Kobayashi, S. J. Am. Chem. Soc., 2000, 122, 11531.
35. Hamada, T., Manabe, K., and Kobayashi, S. Angew. Chem., Int. Ed. Engl. 2003, 42, 3927.
36. Fujii, M., et al. Chem. Express, 1992, 7, 309.
37. Kuwano, R., Miyazaki, H., and Ito, Y. Chem. Commun., 1998, 71.
38. Torii, H., et al. Angew. Chem., Int. Ed. Engl., 2004, 43, 1983.
39. Kobayashi, S., et al. In Science of Synthesis, Houben-Weyl Methods of Molecular Transformation, Vol. 4, Bellus, D., Ley, S.V., Noyori, R., Regitz, M., Schaumann, E., Shinkai, I., Thomas, E.J., and Trost, B.M., Eds., Thieme: New York, 2002, p. 317.
40. Machajewski, T.D. and Wong, C.-H. Angew. Chem., Int. Ed. Engl., 2000, 39, 1352.
41. Carreira, E.M. In Comprehensive Asymmetric Catalysis, Vol. 3, Jacobsen, E.N., Pflatz, A., and Yamamoto, H., Eds., Springer: New York, 1999, p. 998.
42. Nelson, S.G. Tetrahedron: Asymmetry, 1998, 9, 357.
43. Trioxane was used as a formaldehyde surrogate: Mukaiyama, T., Banno, K., and Narasaka, K. J. Am. Chem. Soc., 1974, 96, 7503.
44. For hydroxymethylation of a silicon enolate in aqueous media without any catalysts, see Lubineau, A. and Meyer, E. Tetrahedron, 1988, 44, 6065.
45. Manabe, K., et al. Tetrahedron, 2003, 59, 10439.
46. Ozawa, N., et al. Synlett, 2003, 2219.
47. Ishikawa, S.T., Hamada, T., Manabe, K., Kobayahi, S. J. Am. Chem. Soc., 2004, 126, 12236.
48. Evans, D.A., et al. J. Am. Chem. Soc., 2001, 123, 12095.
49. Evans, D.A., et al. J. Am. Chem. Soc., 2003, 125, 10780.
50. Baliri, P.L., et al. Enantiomer, 1998, 3, 357.
51. Miyaoka, H., et al. Tetrahedron: Asymmetry, 1999, 10, 3189.
52. Gaspard-Iloughmane, H. and Le Roux, C. Eur. J. Org. Chem., 2004, 2517.
53. Répichet, S., et al Tetrahedron Lett., 2002, 43, 993.
54. Kobayashi, S., et al. Synlett, 1993, 472.
55. Kobayashi, S., et al. Org. Lett., 2005, 7, 4729.
56. Ager, D.J., Prakas, H.I., and Schaad, D.R. Chem. Rev., 1996, 96, 835.
57. Bergmeier, S.C. Tetrahedron, 2000, 56, 2561.
58. Yamashita, M., Yamada, K., and Tomioka, K. Org. Lett., 2005, 7, 2369.
59. Kolb, H.C. and Sharpless, K.B. In Transition Metals for Organic Synthesis, Beller, M., Bolm, C., Eds., Wiley-VCH:New York, 1998, p. 243.
60. Hou, X.L., et al. Tetrahedron: Asymmetry, 1998, 9, 1747.
61. Sagawa, S., et al. Org. Chem., 1999, 64, 4962.
62. Sekine, A., Ohshima, T., and Shibasaki, M. Tetrahedron, 2002, 58, 75.
63. Schneider, C., Sreekanth, A.R., and Mai, E. Angew. Chem., Int. Ed. Engl., 2004, 43, 5691.
64. Carrée, F., Gil, R., and Collin, J. Org. Lett., 2005, 7, 1023.
65. Kobayashi, S. and Wakabayashi, T. Tetrahedron Lett., 1998, 39, 5389.
66. Otto, S. and Engberts, J.B.F.N. J. Am. Chem. Soc., 1999, 121, 6798.
67. Sinou, D., Rabeyrin, C., and Nguefack, C. Adv. Synth. Catal., 2003, 345, 357.
68. Azoulay, S., Manabe, K., and Kobayashi, S. Org. Lett., 2005, 7, 4593.
69. Iranpoor, N., Firouzabadi, H., and Shekarize, M. Org. Biomol. Chem., 2003, 1, 724.
70. Fan, R.H. and Hou, X.L. J. Org. Chem., 2003, 68, 726.
71. Ollevier, T. and Lavie-Compain, G. Tetrahedron Lett., 2004, 45, 49.
72. Boudou, M., Ogawa, C., and Kobayashi, S. Adv. Synth. Catal., 2006, 348, 2585.
73. Ogawa, C., Azoulay, S., and Kobayashi, S. Heterocycles 2005, 66, 201.
74. Kobayashi, S. and Ishitani, H. Chem. Rev., 1999, 99, 1069.
75. Taggi, A.E., Hafez, A.M., and Lectka, T. Acc. Chem. Res., 2003, 36, 10.
76. Kobayashi, S. and Ueno, M. In Comprehensive Asymmetric Catalysis, Jacobsen, E.N., Pfaltz, A., Yamamoto, H., Eds., Springer: New York, 2004, supplement 1, chap. 29.5, 143-159.
77. Wolfgang, N., et al. J. Org. Chem., 2003, 68, 9624.
78. Ibrahem, I., Casas, J., and Córdova, A., Angew. Chem., 2004, 116, 6690;
79. Angew. Chem., Int. Ed. Engl. 2004, 43, 6528.
80. Kobayashi, S., Hamada, T., and Manabe, K. J. Am. Chem. Soc. 2002, 124, 5640.
81. Hamada, T., Manabe, K., and Kobayashi, S. J. Am. Chem. Soc., 2004, 126, 7768.
82. Arend, M., Westermann, B., and Risch, N. Angew. Chem., 1998, 110, 1096;
83. Angew. Chem., Int. Ed. Engl., 1998, 37, 1044.
84. Burk, M.J. and Feaster, J.E. J. Am. Chem. Soc., 1992, 114, 6266.
85. Oyamada, H. and Kobayashi, S. Synlett, 1998, 249.
86. Kobayashi, S., Sugita, K., and Oyamada, H. Synlett, 1999, 138.
87. Manabe, K., et al. J. Org. Chem., 1999, 64, 8054.
88. Kobayashi, S., Hasegawa, Y., and Ishitani, H. Chem. Lett., 1998, 1131.
89. Hydrazine and its derivatives, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed., Wiley & Sons: New York, 1995, vol. 13.
90. Kobayashi, S., Hamada, T., and Manabe, K. Synlett 2001, 1140.
91. Hamada, T., et al. J. Am. Chem. Soc., 2003, 125, 2989.
92. Hamada, T., Manabe, K., and Kobayashi, S., Chem. Eur. J., 2006, 12, 1205.