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Chiral phase transfer catalysis

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Book cover Handbook of Phase Transfer Catalysis

Abstract

Phase transfer catalysis has now become a very important method for synthetic organic reactions. The catalysts utilized for phase transfer catalysis are, in general, not expensive, are easy to prepare and can be used for large- scale reactions. If the desired reactions proceed sluggishly, addition of a small amount of a phase transfer catalyst might accelerate the reactions in a number of cases. However, asymmetric reactions utilizing chiral phase transfer catalysts still remain to be investigated further, in contrast to reacĀ­tions with the use of achiral phase transfer catalysts. Since excellent reviews on the same subject covering the literature up to 1991 have already appeared [1-3], emphasis will be put on more recent work. However, earlier important results will also be mentioned.

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References

  1. Oā€™Donnell, M.J. (1993) in Catalytic Asymmetric Synthesis (ed. I. Ojima), VCH, New York, Chapter 8, pp. 389ā€“411.

    Google ScholarĀ 

  2. Dehmlow, E.V. and Dehmlow, S.S. (1993) Phase Transfer Catalysis, VCH, New York, Section 3.1.5.

    Google ScholarĀ 

  3. Starks, C.M., Liotta, C. L. and Halpern, M. (1994) Phase-Transfer Catalysis. Fundamentals, Applications, and Industrial Perspectives, Chapman & Hall, New York, Chapter 12.

    Google ScholarĀ 

  4. Ando, A., Miura, T., Tatematsu, T. and Shioiri, T. (1993) Tetrahedron Lett., 34, 1507ā€“10.

    ArticleĀ  CASĀ  Google ScholarĀ 

  5. Shioiri, T., Bohsako, A. and Ando, A. (1996) Heterocycles, 42, 93ā€“7.

    ArticleĀ  CASĀ  Google ScholarĀ 

  6. Dolling, U.-H., Davis, P. and Grabowski, E.J.J. (1984) J Am. Chem. Soc., 106,446ā€“7.

    ArticleĀ  CASĀ  Google ScholarĀ 

  7. Bhattacharya, A., Dolling, U.-H., Grabowski, E.J.J, et al. (1986) Angew Chem., Int. Ed Engl., IS, 476ā€“7.

    Google ScholarĀ 

  8. Hughes, D.L., Dolling, U.-H., Ryan, K.M. et al. (1987)J Org. Chem., 52,4745ā€“52.

    ArticleĀ  CASĀ  Google ScholarĀ 

  9. Nerinckx, W. and Vandewalle, M. (1990) Tetrahedron: Asymmetry, 1, 265ā€“76.

    ArticleĀ  CASĀ  Google ScholarĀ 

  10. Masui, M., Ando, A. and Shioiri, T. (1988) Tetrahedron Lett., 29, 2835ā€“8.

    ArticleĀ  CASĀ  Google ScholarĀ 

  11. Lee, T.B.K. and Wong, G.S.K. (1991)J. Org. Chem., 56, 872ā€“5.

    Google ScholarĀ 

  12. Oā€™Donnell, M.J., Bennett, W.D. and Wu, S. (1989)J Am. Chem. Soc., Ill, 2353ā€“5.

    Google ScholarĀ 

  13. Tohdo, K., Hamada, Y. and Shioiri, T. (1992) in Peptide Chemistry 1991 (ed. A. Suzuki), Protein Research Foundation, Osaka, pp. 7ā€“12.

    Google ScholarĀ 

  14. Tohdo, K., Hamada, Y. and Shioiri, T. (1994) Synlett, 247ā€“9.

    Google ScholarĀ 

  15. Imperiali, B. and Fisher, S.L. (1992) J. Org. Chem., 57, 757ā€“9.

    ArticleĀ  CASĀ  Google ScholarĀ 

  16. Imperiali, B., Prins, T.J. and Fisher, S.L. (1993)J Org. Chem., 58, 1613ā€“6.

    Google ScholarĀ 

  17. Oā€™Donnell, M.J. and Wu, S. (1992) Tetrahedron: Asymmetry, 3, 591-4.

    Google ScholarĀ 

  18. Dehmlow, E.V. and Knufinke, V. (1992) Liebigs Ann. Chem., 283ā€“5.

    Google ScholarĀ 

  19. Lipkowitz, K.B., Cavanaugh, M.W., Baker, B. and Oā€™Donnell, M.J. (1991) J. Org. Chem., 56,5181ā€“92.

    ArticleĀ  CASĀ  Google ScholarĀ 

  20. Oā€™Donnell, M.J., Wu, S. and Huffman, J.C. (1994) Tetrahedron, 50,4507ā€“18.

    Google ScholarĀ 

  21. Esikova, I., Nahreini, T. and Oā€™Donnell, M.J. (1995) in Abstracts of 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, Part 2, Section 9, No. 725.

    Google ScholarĀ 

  22. Oā€™Donnell, M.J., Esikova, I., Fang, Z. et al. (1995) in Abstracts of 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, Part 2, Section 9, No. 1128.

    Google ScholarĀ 

  23. Jamal Eddine, J. and Cherqaoui, M. (1995) Tetrahedron: Asymmetry, 6, 1225ā€“8.

    Google ScholarĀ 

  24. Asai, T., Aoyama, T. and Shioiri, T. (1980) Synthesis, 811ā€“2.

    Google ScholarĀ 

  25. Shioiri, T. (1995) in Abstracts of 1995 International Chemical Congress of Pacific Basin Societies, Honolulu, Part 2, Section 9, No. 990.

    Google ScholarĀ 

  26. Bohsako, A., Asakura, C. and Shioiri, T. (1995) Synlett., 1033-4.

    Google ScholarĀ 

  27. Soai, K. and Watanabe, M. (1990) J Chem. Soc., Chem. Commun., 43ā€“4.

    Google ScholarĀ 

  28. Iseki, K., Nagai, T. and Kobayashi, Y. (1994) Tetrahedron Lett., 35, 3137ā€“8.

    ArticleĀ  CASĀ  Google ScholarĀ 

  29. Cram, D.J. and Sogah, G.D.Y. (1981) J Chem. Soc., Chem. Commun., 625ā€“8.

    Google ScholarĀ 

  30. Takasu, M., Wakabayashi, H., Furuta, K. and Yamamoto, H. (1988) Tetrahedron Lett., 29, 6943ā€“6.

    ArticleĀ  CASĀ  Google ScholarĀ 

  31. Aoki, S., Sasaki, S. and Koga, K. (1989) Tetrahedron Lett., 30, 7229ā€“30.

    ArticleĀ  CASĀ  Google ScholarĀ 

  32. Brunet, E., Poveda, A.M., Rabasco, D. et al. (1994) Tetrahedron: Asymmetry, 5, 935ā€“48.

    ArticleĀ  CASĀ  Google ScholarĀ 

  33. Conn, R.S.E., Lovell, A.V., Karady, S. and Weinstock, L.M. (1986) J. Org. Chem., 51, 4710ā€“1.

    ArticleĀ  CASĀ  Google ScholarĀ 

  34. Shishido, K., Takaishi, Y., Wariishi, N. et al. (1992) in Abstracts of the 34th Symposium on the Chemistry of Natural Products, Japan, pp. 352ā€“9; Chem. Abstr., 1994,120, 173182.

    Google ScholarĀ 

  35. Aoki, S., Sasaki, S. and Koga, K. (1992) Heterocycles, 33,493ā€“5.

    ArticleĀ  CASĀ  Google ScholarĀ 

  36. Dehmlow, E.V. and Schrader, S. (1994) Pol. J. Chem., 68, 2199ā€“208.

    CASĀ  Google ScholarĀ 

  37. Shi, M. and Masaki, Y. (1994) J. Chem. Res. (S), 250ā€“1; (M), 1460ā€“76.

    Google ScholarĀ 

  38. Shi, M., Kazuta, K., Satoh, Y. and Masaki, Y. (1994) Chem. Pharm. Bull., 42, 2625ā€“8.

    CASĀ  Google ScholarĀ 

  39. Shi, M., Itoh, N. and Masaki, Y. (1995)J Chem. Res. (S), 46ā€“7; (M), 0401ā€“11.

    Google ScholarĀ 

  40. Chang, S., Galvin, J.M. and Jacobsen, E.N. (1994) J. Am. Chem. Soc., 116, 6937ā€“8.

    ArticleĀ  CASĀ  Google ScholarĀ 

  41. de Vries, E.F.J., Ploeg, L., Colao, M. et al. (1995) Tetrahedron: Asymmetry, 6, 1123ā€“32.

    ArticleĀ  Google ScholarĀ 

  42. Passarotti, C., Bandi, G.L., Fossati, A. et al. (1990) Boll. Chim. Farm., 129, 195ā€“8.

    CASĀ  Google ScholarĀ 

  43. Takeshita, M., Yanagihara, H., Terada, K. and Akutsu, N. (1992) Annu. Rep. Tohoku Coll Pharm., 39, 247ā€“50; Chem. Abstr., 1994,120, 244600.

    Google ScholarĀ 

  44. Adjidjonou, K. and Caze, C. (1994) Eur. Polym. J., 30, 395ā€“8; Chem. Abstr., 121, 8776v.

    Google ScholarĀ 

  45. Guifa, S. and Lingchong, Y. (1993) Synth. Commun., 23, 1229ā€“34.

    ArticleĀ  Google ScholarĀ 

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Ā© 1997 Chapman & Hall

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Shioiri, T. (1997). Chiral phase transfer catalysis. In: Sasson, Y., Neumann, R. (eds) Handbook of Phase Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0023-3_14

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  • DOI: https://doi.org/10.1007/978-94-009-0023-3_14

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7514-0258-2

  • Online ISBN: 978-94-009-0023-3

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