Binaphthyl-and Biphenyl-Modified Chiral Phase-Transfer Catalysts for Asymmetric Synthesis

Asymmetric Phase Transfer Catalysis

Volumn , Issue , 2008, Pages 71-113

  Maruoka, Keiji ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Binaphthyl modified; Biphenyl modified; Epoxidation; N spiro chiral ammonium salts; Neber rearrangement; Quaternary ammonium salts; Strecker reaction

Indexed keywords

EID: 84885720862     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527622627.ch5     Document Type: Chapter

References (99)

1. Dehmlow, E.V. and Dehmlow, S.S. (1993) Phase Transfer Catalysis, 3rd edn. VCH Weinheim;
2. Starks, C.M., Liotta, C.L. and Halpern, M. (1994) Phase-Transfer Catalysis, Chapman & Hall, New York;
3. Sasson, Y. and Neumann, R. (1997) Handbook of Phase-Transfer Catalysis, Blackie Academic & Professional, London;
4. Halpern, M.E. (1997) Phase-Transfer Catalysis. ACS Symposium Series 659, American Chemical Society, Washington, DC.
5. Shioiri, T. (1997) Handbook of Phase-Transfer Catalysis (eds Y. Sasson and R. Neumann), Blackie Academic & Professional, Chapter 14;
6. O'Donnell, M.J. (1998) Phases-The Sachem Phase Transfer Catalysis Review (4), 5;
7. O'Donnell, M.J. (1999) Phases-The Sachem Phase Transfer Catalysis Review (5), 5;
8. Nelson, A. (1999) Angew. Chem., Int. Ed., 38, 1583;
9. Shioiri, T. and Arai, S. (2000) Stimulating Concepts in Chemistry, (eds F. Vogtle, J.F. Stoddart and M. Shibasaki), Wiley-VCHWeinheim, p. 123;
10. O'Donnell, M.J. (2000) Catalytic Asymmetric Syntheses, 2nd edn. (ed. I. Ojima), Wiley-VCH, London, New York, Chapter 10;
11. O'Donnell, M.J. (2001) Aldrichimica Acta, 34, 3;
12. Maruoka, K. and Ooi, T. (2003) Chem. Rev., 103, 3013;
13. O'Donnell, M.J. (2004) Acc. Chem. Res., 37, 506;
14. Lygo, B. and Andrews, B.I. (2004) Acc. Chem. Res., 37, 518;
15. Vachon, J. and Lacour, J. (2006) Chimia, 60, 266;
16. Maruoka, K., Ooi, T. and Kano, T. (2007) Chem. Commun, 1487;
17. Ooi, T. and Maruoka, K. (2007) Angew. Chem., Int. Ed., 46, 4222;
18. Maruoka, K. (2007) CHIMIA, 61, 263;
19. Ooi, T. and Maruoka, K. (2007) Aldrichimica Acta, 40, 77.
20. Dolling, U.-H., Davis, P. and Grabowski, E.J.J. (1984) J. Am. Chem. Soc., 106, 446;
21. Hughes, D.L., Dolling, U.-H., Ryan, K.M., Schoenewaldt, E.F. and Grabowski, E.J.J. (1987) J. Org. Chem., 52, 4745.
22. O'Donnell, M.J., Bennett, W.D. and Wu, S. (1989) J. Am. Chem. Soc., 111, 2353;
23. Lipkowitz, K.B., Cavanaugh, M.W., Baker, B. and O'Donnell, M.J. (1991) J. Org. Chem., 56, 5181;
24. Esikova, I.A., Nahreini, T.S. and O'Donnell, M.J. (1997) Phase-Transfer Catalysis (ed. M.E. Halpern), ACS Symposium Series 659, American Chemical Society, Washington, DC, Chapter 7;
25. O'Donnell, M.J., Esikova, I.A., Shullenberger, D.F. and Wu, S. (1997) Phase-Transfer Catalysis (ed. M.E. Halpern), ACS Symposium Series 659, American Chemical Society, Washington, DC, Chapter 10.
26. Lygo, B. and Wainwright, P.G. (1997) Tetrahedron Lett., 38, 8595;
27. Lygo, B., Crosby, J., Lowdon, T.R. and Wainwright, P.G. (2001) Tetrahedron, 57, 2391;
28. Lygo, B., Crosby, J., Lowdon, T.R., Peterson, J.A. and Wainwright, P.G. (2001) Tetrahedron, 57, 2403;
29. Lygo, B., Andrews, B.I., Crosby, J. and Peterson, J.A. (2002) Tetrahedron Lett., 43, 8015.
30. Corey, E.J., Xu, F. and Noe, M.C. (1997) J. Am. Chem. Soc., 119, 12414.
31. Ooi, T., Kameda, M. and Maruoka, K. (1999) J. Am. Chem. Soc., 121, 6519;
32. Maruoka, K. (2001) J. Fluorine Chem., 112, 95;
33. Ooi, T., Uematsu, Y. and Maruoka, K. (2002) Adv. Synth. Catal., 344, 288;
34. Ooi, T., Uematsu, Y. and Maruoka, K. (2003) J. Org. Chem., 68, 4576;
35. Ooi, T., Kameda, M. and Maruoka, K. (2003) J. Am. Chem. Soc., 125, 5139.
36. Ooi, T., Uematsu, Y. and Maruoka, K. (2004) Tetrahedron Lett., 45, 1675.
37. Hashimoto, T. and Maruoka, K. (2003) Tetrahedron Lett., 44, 3313;
38. Hashimoto, T., Tanaka, Y. and Maruoka, K. (2003) Tetrahedron: Asymmetry, 14, 1599.
39. Ooi, T., Tayama, E., Doda, K., Takeuchi, M. and Maruoka, K. (2000) Synlett, 1500.
40. Shirakawa, S., Yamamoto, K., Kitamura, M., Ooi, T. and Maruoka, K. (2005) Angew. Chem., Int. Ed., 44, 625.
41. Ooi, T., Uematsu, Y., Kameda, M. and Maruoka, K. (2002) Angew. Chem., Int. Ed., 41, 1551;
42. Ooi, T., Uematsu, Y., Kameda, M. and Maruoka, K. (2006) Tetrahedron, 62, 11425.
43. Kano, T., Konishi, S., Shirakawa, S. and Maruoka, K. (2004) Tetrahedron:Asymmetry, 15, 1243.
44. Kitamura, M., Shirakawa, S. and Maruoka, K. (2005) Angew. Chem., Int. Ed., 44, 1549.
45. Ooi, T., Kubota, Y. and Maruoka, K. (2003) Synlett, 1931.
46. Han, Z., Yamaguchi, Y., Kitamura, M. and Maruoka, K. (2005) Tetrahedron Lett., 46, 8555;
47. Wang, Y.-G., Ueda, M., Wang, X., Han, Z. and Maruoka, K. (2007) Tetrahedron, 63, 6042.
48. Wang, Y.-G. and Maruoka, K. (2007) Org. Process Res. Dev., 11, 628. (see also Ref. 16b).
49. O'Donnell, M.J. and Wu, S. (1992) Tetrahedron: Asymmetry, 3, 591;
50. Belokon, Y.N., Kochetkov, K.A., Churkina, T.D., Ikonnikov, N.S., Chesnokov, A.A., Larionov, O.V., Parmar, V.S., Kumar, R. and Kagan, H.B. (1998) Tetrahedron:Asymmetry, 9, 851;
51. Lygo, B., Crosby, J. and Peterson, J.A. (1999) Tetrahedron Lett., 40, 8671;
52. Belokon, Y.N., Kochetkov, K.A., Churkina, T.D., Ikonnikov, N.S., Vyskocil, S. and Kagan, H.B. (1999) Tetrahedron: Asymmetry, 10, 1723;
53. Belokon, Y.N., North, M., Kublitski, V.S., Ikonnikov, N.S., Krasik, P.E. and Maleev, V.I. (1999) Tetrahedron Lett., 40, 6105;
54. Belokon, Y.N., Kochetkov, K.A., Churkina, T.D., Ikonnikov, N.S., Chesnokov, A.A., Larionov, O.V., Singh, I., Parmar, V.S., Vyskocil, S. and Kagan, H.B. (2000) J. Org. Chem., 65, 7041;
55. Belokon, Y.N., Davies, R.G. and North, M. (2000) Tetrahedron Lett., 41, 7245;
56. Belokon, Y.N., Davies, R.G., Fuentes, J.A., North, M. and Parsons, T. (2001) Tetrahedron Lett., 42, 8093;
57. Belokon, Y.N., Bhave, D., D'Addario, D., Groaz, E., North, M. and Tagliazucca, V. (2004) Tetrahedron, 60, 1849;
58. Belokon, Y.N., Fuentes, J.A., North, M. and Steed, J.W. (2004) Tetrahedron, 60, 3191;
59. Elango, S., Venugopal, M., Suresh, P.S. and Elango, E. (2005) Tetrahedron, 61, 1443.
60. Ooi, T., Takeuchi, M., Kameda, M. and Maruoka, K. (2000) J. Am. Chem. Soc., 122, 5228.
61. Ooi, T., Arimura, Y., Hiraiwa, Y., Yuan, L.M., Kano, T., Inoue, T., Matsumoto, J. and Maruoka, K. (2006) Tetrahedron:Asymmetry, 17, 608.
62. Ooi, T., Sakai, D., Takeuchi, M., Tayama, E. and Maruoka, K. (2003) Angew. Chem., Int. Ed., 42, 5868.
63. Ooi, T., Takeuchi, M., Kato, D., Uematsu, Y., Tayama, E., Sakai, D. and Maruoka, K. (2005) J. Am. Chem. Soc., 127, 5073.
64. Shirakawa, S., Tanaka, Y. and Maruoka, K. (2004) Org. Lett., 6, 1429.
65. Ooi, T., Kameda, M., Tannai, H. and Maruoka, K. (2000) Tetrahedron Lett., 41, 8339.
66. Ooi, T., Takeuchi, M. and Maruoka, K. (2001) Synthesis, 1716.
67. Vogt, H. and Bräse, S. (2007) Org. Biomol. Chem., 5, 406;
68. Ohfune, Y., Shinada, T. (2005) Eur. J. Org. Chem. 5127;
69. Cativiela, C. and Diaz-de-Villegas, M.D. (1998) Tetrahedron: Asymmetry, 9, 3517;
70. Schöllkopf, U. (1983) Top. Curr. Chem., 109, 65.
71. Maeda, K., Miller, R.A., Szumigala, R.H. Jr., Shafiee, A., Karady, S. and Armstrong, J.D. III (2005) Tetrahedron Lett., 46, 1545.
72. Jew, S.-s., Lee, Y.-J., Lee, J., Kang, M.J., Jeong, B.-S., Lee, J.-H., Yoo, M.-S., Kim, M.-J., Choi, S.-h., Ku, J.-M. and Park, H.-g. (2004) Angew. Chem., Int. Ed., 43, 2382.
73. Kim, T.-S., Lee, Y.-J., Jeong, B.-S., Park, H.-g. and Jew, S.-s. (2006) J. Org. Chem., 71, 8276.
74. For a comprehensive review on the use of peptide enolates, see: Seebach, D., Beck, A.K. and Studer, A. (1995) Modern Synthetic Methods (eds B. Ernst and C. Leumann), VCH, Weinheim, Vol. 7, p. 1.
75. Ooi, T., Tayama, E. and Maruoka, K. (2003) Angew. Chem., Int. Ed., 42, 579;
76. Maruoka, K., Tayama, E. and Ooi, T. (2004) Proc. Natl. Acad. Sci. USA, 101, 5824.
77. Ooi, T., Miki, T., Taniguchi, M., Shiraishi, M., Takeuchi, M. and Maruoka, K. (2003) Angew. Chem., Int. Ed., 42, 3796;
78. Ooi, T., Miki, T., Fukumoto, K. and Maruoka, K. (2006) Adv. Synth. Catal., 348, 1539.
79. Ooi, T., Miki, T. and Maruoka, K. (2005) Org. Lett., 7, 191.
80. Nogata, K., Sano, D. and Itoh, T. (2007) Synlett 547.
81. Ooi, T., Fukumoto, K. and Maruoka, K. (2006) Angew. Chem., Int. Ed., 45, 3839.
82. For recent reviews on catalytic asymmetric Michael reactions, see: Krause, N. and Hoffman-Röder, A. (2001) Synthesis, 171;
83. Sibi, M. and Manyem, S. (2000) Tetrahedron, 56, 8033;
84. Kanai, M. and Shibasaki, M. (2000) Catalytic Asymmetric Synthesis (ed. I. Ojima), Wiley, p. 569;
85. Tomioka, K. and Nagaoka, Y. (1999) Comprehensive Asymmetric Catalysis, 2nd edn. (eds E.N. Jacobsen, A. Pfaltz and H. Yamamoto), Vol. 3, Springer, New York, Berlin. Chapter 31.1.
86. Ooi, T., Ohara, D., Fukumoto, K. and Maruoka, K. (2005) Org. Lett., 7, 3195.
87. Lee, Y.-J., Lee, J., Kim, M.-J., Jeong, B.-S., Lee, J.-H., Kim, T.-S., Lee, J., Ku, J.-M., Jew, S.-s. and Park, H.-g. (2005) Org. Lett., 7, 3207.
88. Ooi, T., Fujioka, S. and Maruoka, K. (2004) J. Am. Chem. Soc., 126, 11790;
89. Ooi, T., Takada, S., Fujioka, S. and Maruoka, K. (2005) Org. Lett., 7, 5143.
90. Wang, X., Kitamura, M. and Maruoka, K. (2007) J. Am. Chem. Soc., 129, 1038.
91. Ooi, T., Taniguchi, M., Kameda, M. and Maruoka, K. (2002) Angew. Chem., Int. Ed., 41, 4542;
92. Ooi, T., Kameda, M., Taniguchi, M. and Maruoka, K. (2004) J. Am. Chem. Soc., 126, 9685.
93. Ooi, T., Kameda, M., Fujii, J. and Maruoka, K. (2004) Org. Lett., 6, 2397.
94. Ooi, T., Takahashi, M., Doda, K. and Maruoka, K. (2002) J. Am. Chem. Soc., 124, 7640.
95. For reviews, see: Porter, M.J. and Skidmore, J. (2000) Chem. Commun., 1215;
96. Nemoto, T., Ohshima, T. and Shibasaki, M. (2002) J. Synth. Org. Chem. Jpn., 60, 94.
97. Ooi, T., Ohara, D., Tamura, M. and Maruoka, K. (2004) J. Am. Chem. Soc., 126, 6844.
98. Ooi, T., Uematsu, Y. and Maruoka, K. (2006) J. Am. Chem. Soc., 128, 2548;
99. Ooi, T., Uematsu, Y., Fujumoto, J., Fukumoto, K. and Maruoka, K. (2007) Tetrahedron Lett., 48, 1337.