Domino Reactions Involving Catalytic Enantioselective Conjugate Additions

Catalytic Asymmetric Conjugate Reactions

Volumn , Issue , 2010, Pages 321-350

  Tietze, Lutz F ^a   Düfert, Alexander ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Aldol reactions; Domino reactions; Enantioselective transformations; Michael additions; Organocatalysis; Transition metal catalysis

Indexed keywords

EID: 84887151171     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527630578.ch8     Document Type: Chapter

References (100)

1. Tietze, L.F. and Beifuss, U. (1993) Angew. Chem., 105, 137-170;
2. Tietze, L.F. and Beifuss, U. (1993) Angew. Chem., Int. Ed. Engl., 32, 131-163;
3. Tietze, L.F. (1996) Chem. Rev., 96, 115-136;
4. Tietze, L.F. and Rackelmann, N. (2004) Pure Appl. Chem., 76, 1933-1983;
5. Tietze, L.F. and Rackelmann, N. (2005) in Multicomponent Reactions (ed. J. Zhu), Wiley-VCH Verlag GmbH, Weinheim;
6. Tietze, L.F., Brasche, G., and Gericke, K. (2006) Domino Reactions in Organic Synthesis, Wiley-VCH Verlag GmbH, Weinheim;
7. Tietze, L.F. and Levy, L. (2009) in The Mizoroki-Heck Reaction (ed. M. Oestreich), Wiley-VCH Verlag GmbH, Chichester, pp. 281-344;
8. Tietze, L.F., Kinzel, T., and Brazel, C. (2009) Acc. Chem. Res., 42, 367-378;
9. Tietze, L.F., Spiegl, D.A., and Brazel, C.C. (2009) in Experiments in Green and Sustainable Chemistry (ed. H.W. Roesky and D.K. Kennepohl), Wiley-VCH Verlag GmbH, Weinheim, pp. 158-167.
10. Tomioka, K. and Nagaoka, Y. (1999) in Comprehensive Asymmetric Catalysis I-III, vol. 3 (eds E.N. Jacobsen, A. Pfaltz, and H. Yamamoto), Springer, Berlin, pp. 1105-1120;
11. Guo, H.-C. and Ma, J.-A. (2006) Angew. Chem., Int. Ed., 45, 354-366.
12. Kataoka, T. and Kinoshita, H. (2005) Eur. J. Org. Chem., 45-58.
13. Palomo, C., Oiarbide, M., and Garcia, J.M. (2004) Chem. Soc. Rev., 33, 65-75;
14. Machajewski, T.D., Wong, C.-H., and Lerner, R.A. (2000) Angew. Chem., Int. Ed., 39, 1352-1374.
15. Yamada, K., Arai, T., Sasai, H., and Shibasaki, M. (1998) J. Org. Chem., 63, 3666-3672.
16. Shibasaki, M., Sasai, H., and Arai, T. (1997) Angew. Chem., Int. Ed. Engl., 36, 1237-1256, and references cited therein.
17. Arai, T., Sasai, H., Aoe, K., Okamura, K., Date, T., and Shibasaki, M. (1996) Angew. Chem., Int. Ed. Engl., 35, 104-106.
18. Thaler, T. and Knochel, P. (2009) Angew. Chem., Int. Ed., 48, 645-648;
19. Alexakis, A., Bäckvall, J.E., Krause, N., Pàmies, O., and Diéguez, M. (2008) Chem. Rev., 108, 2796-2823;
20. Breit, B. and Schmidt, Y. (2008) Chem. Rev., 108, 2928-2951.
21. Arnold, L.A., Naasz, R., Minnaard, A.J., and Feringa, B.L. (2002) J. Org. Chem., 67, 7244-7254.
22. Feringa, B.L. (2000) Acc. Chem. Res., 33, 346-353.
23. Arnold, L.A., Naasz, R., Minnaard, A.J., and Feringa, B.L. (2001) J. Am. Chem. Soc., 123, 5841-5842.
24. Agapiou, K., Cauble, D.F., and Krische, M.J. (2004) J. Am. Chem. Soc., 126, 4528-4529.
25. Xu, Y.-J., Liu, Q.-Z., and Dong, L. (2007) Synlett, 273-277.
26. Oisaki, K., Zhao, D., Kanai, M., and Shibasaki, M. (2007) J. Am. Chem. Soc., 129, 7439-7443.
27. Lipshutz, B. (2009) Synlett, 509-524;
28. Deutsch, C., Krause, N., and Lipshutz, B.H. (2008) Chem. Rev., 108, 2916-2927.
29. Mahoney, W.S., Brestensky, D.M., and Stryker, J.M. (1988) J. Am. Chem. Soc., 110, 291-293.
30. Rendler, S. and Oestreich, M. (2007) Angew. Chem., Int. Ed., 46, 498-504.
31. Lam, H.W. and Joensuu, P.M. (2005) Org. Lett., 7, 4225-4228.
32. Deschamp, J., Chuzel, O., Hannedouche, J., and Riant, O. (2006) Angew. Chem., Int. Ed., 45, 1292-1297.
33. Zhao, D., Oisaki, K., Kanai, M., and Shibasaki, M. (2006) Tetrahedron Lett., 47, 1403-1407.
34. Lipshutz, B.H., Amorelli, B., and Unger, J.B. (2008) J. Am. Chem. Soc., 130, 14378-14379.
35. Hayashi, T. and Yamasaki, K. (2003) Chem. Rev., 103, 2829-2844.
36. Taylor, S.J., Duffey, M.O., and Morken, J.P. (2000) J. Am. Chem. Soc., 122, 4528-4529.
37. Russell, A.E., Fuller, N.O., Taylor, S.J., Aurriset, P., and Morken, J.P. (2004) Org. Lett., 6, 2309-2312.
38. Nicolaou, K.C., Tang, W., Dagneau, P., and Faraoni, R. (2005) Angew. Chem., Int. Ed., 44, 3874-3879.
39. Cauble, D.F., Gipson, J.D., and Krische, M.J. (2003) J. Am. Chem. Soc., 125, 1110-1111.
40. Hayashi, T., Takahashi, M., Takaya, Y., and Ogasawara, M. (2002) J. Am. Chem. Soc., 124, 5052-5058.
41. Bocknack, B.M., Wang, L.-C., and Krische, M.J. (2004) Proc. Natl Acad. Sci. USA, 101, 5421-5424.
42. Zhao, C.-X., Duffey, M.O., Taylor, S.J., and Morken, J.P. (2001) Org. Lett., 3, 1829-1831.
43. van Lingen, H.L., Zhuang, W., Hansen, T., Rutjes, F.P.J.T., and Jørgensen, K.A. (2003) Org. Biomol. Chem., 1, 1953-1958.
44. Lyle, M.P.A., Draper, N.D., and Wilson, P.D. (2005) Org. Lett., 7, 901-904.
45. Naasz, R., Arnold, L.A., Pineschi, M., Keller, E., and Feringa, B.L. (1999) J. Am. Chem. Soc., 121, 1104-1105;
46. Sibi, M.P. and Chen, J. (2001) J. Am. Chem. Soc., 123, 9472-9473;
47. Hayashi, T., Tokunaga, N., Yoshida, K., and Han, J.W. (2002) J. Am. Chem. Soc., 124, 12102-12103;
48. Shintani, R., Tokunaga, N., Doi, H., and Hayashi, T. (2004) J. Am. Chem. Soc., 126, 6240-6241;
49. Rathgeb, X., March, S., and Alexakis, A. (2006) J. Org. Chem., 71, 5737-5742;
50. Šebesta, R., Pizzuti, M.G., Minnaard, A.J., and Feringa, B.L. (2007) Adv. Synth. Catal., 349, 1931-1937.
51. Dijk, E.W., Panella, L., Pinho, P., Naasz, R., Meetsma, A., Minnaard, A.J., and Feringa, B.L. (2004) Tetrahedron, 60, 9687-9693.
52. Alexakis, A., Trevitt, G.P., and Bernardinelli, G. (2001) J. Am. Chem. Soc., 123, 4358-4359.
53. Brown, M.K. and Hoveyda, A.H. (2008) J. Am. Chem. Soc., 130, 12904-12906.
54. Brown, M.K., May, T.L., Baxter, C.A., and Hoveyda, A.H. (2007) Angew. Chem., Int. Ed., 46, 1097-1100;
55. May, T.L., Brown, M.K., and Hoveyda, A.H. (2008) Angew. Chem., Int. Ed., 47, 7358-7362.
56. Knopff, O. and Alexakis, A. (2002) Org. Lett., 4, 3835-3837.
57. Alexakis, A. and March, S. (2002) J. Org. Chem., 67, 8753-8757.
58. Doyle, A.G. and Jacobsen, E.N. (2007) Chem. Rev., 107, 5713-5743.
59. Mukherjee, S., Yang, J.W., Hoffmann, S., and List, B. (2007) Chem. Rev., 107, 5471-5569;
60. Erkkil, A., Majander, I., and Pihko, P.M. (2007) Chem. Rev., 107, 5471-5569.
61. Kaneko, S., Yoshino, T., Katoh, T., and Terashima, S. (1998) Tetrahedron Lett., 54, 5471-5484.
62. Corn, R.S.E., Lovell, A.V., Karady, S., and Weinstock, L.M. (1986) J. Org. Chem., 51, 4710-4711;
63. Takagi, K., Katayama, H., and Yamada, H. (1988) J. Org. Chem., 53, 1157-1161.
64. Betancort, J.M., Sakthivel, K., Thayumanavan, R., and Barbas, C.F.III (2001) Tetrahedron. Lett., 42, 4441-4444.
65. Yamamoto, Y., Momiyama, N., and Yamamoto, H. (2004) J. Am. Chem. Soc., 126, 5962-5963.
66. Li, H., Wang, J., Xie, H., Zu, L., Jiang, W., Duesler, E.N., and Wang, W. (2007) Org. Lett., 9, 965-968.
67. Sundén, H., Ibrahem, I., Eriksson, L., and Córdova, A. (2005) Angew. Chem., Int. Ed., 44, 4877-4880.
68. Carlone, A., Marigo, M., North, C., Landa, A., and Jørgensen, K.A. (2006) Chem. Commun., 4928-4930.
69. Zhou, J. and List, B. (2007) J. Am. Chem. Soc., 129, 7498-7499.
70. Wang, J., Yu, F., Zhang, X., and Ma, D. (2008) Org. Lett., 10, 2561-2564.
71. Penon, O., Carlone, A., Mazzanti, A., Locatelli, M., Sambri, L., Bartoli, G., and Melchiorre, P. (2008) Chem. Eur. J., 14, 4788-4791.
72. Valero, G., Schimer, J., Cisarova, I., Vesely, J., Moyano, A., and Rios, R. (2009) Tetrahedron Lett., 50, 1943-1946.
73. Halland, N., Aburel, P.S., and Jørgensen, K.A. (2004) Angew. Chem., Int. Ed., 43, 1272-1277.
74. Eder, U., Sauer, G., and Wiechert, R. (1971) Angew. Chem., Int. Ed. Engl., 10, 496-497;
75. Hajos, Z.G. and Parrish, D.R. (1974) J. Org. Chem., 39, 1615-1621; see also:
76. Arai, T., Sasai, H., Aoe, K.-I., Okamura, K., Date, T., and Shibasaki, M. (1996) Angew. Chem., Int. Ed. Engl., 35, 104-106;
77. Bui, T. and Barbas, C.F. III (2000) Tetrahedron Lett., 41, 6951-6954.
78. Marigo, M., Schulte, T., Franzén, J., and Jørgensen, K.A. (2005) J. Am. Chem. Soc., 127, 15710-15711;
79. Huang, Y., Walji, A.M., Larsen, C.H., and MacMillan, D.W.C. (2005) J. Am. Chem. Soc., 127, 15051-15053.
80. Simmons, B., Walji, A.B., and MacMillan, D.W.C. (2009) Angew. Chem., Int. Ed., 48, 4349-4353.
81. Carle, J.S. and Chrisophersen, C. (1981) J. Org. Chem., 46, 3440-3443;
82. Carle, J.S. and Chrisophersen, C. (1980) J. Org. Chem., 45, 1586-1589;
83. Carle, J.S. and Chrisophersen, C. (1979) J. Am. Chem. Soc., 101, 4012-4013.
84. Austin, J.F., Kim, S.-G., Sinz, C.J., Xiao, W.-J., and MacMillan, D.W.C. (2004) Proc. Natl Acad. Sci. USA, 101, 5482-5487.
85. Franzén, J. and Fisher, A. (2009) Angew. Chem., Int. Ed., 48, 787-791.
86. Franzén, H., Rios, R., Ibrahem, I., Zhao, G.-L., Eriksson, L., and Córdova, A. (2007) Adv. Synth. Catal., 349, 827-832.
87. Sundén, H., Ibrahem, I., Zhao, G.-L., Eriksson, L., and Córdova, A. (2007) Chem. Eur. J., 13, 574-581.
88. Rueping, M., Sugiono, E., and Merino, E. (2008) Angew. Chem., Int. Ed., 47, 3046-3049.
89. Rios, R., Sundén, H., Ibrahem, I., and Córdova, A. (2007) Tetrahedron Lett., 48, 2181-2184.
90. Rueping, M., Kuenkel, A., Tato, F., and Bats, J.W. (2009) Angew. Chem., Int. Ed., 48, 3699-3702.
91. Enders, D., Hüttl, M.R.M., Grondal, C., and Raabe, G. (2006) Nature, 441, 861-863.
92. Ibrahem, I., Rios, R., Vesely, J., Zhao, G.-L., and Córdova, A. (2007) Chem. Commun., 13, 849-851.
93. Jiang, H., Elsner, P., Jensen, K.L., Falcicchio, A., Marcos, V., and Jørgensen, K.A. (2009) Angew. Chem., Int. Ed., 48, 6844-6848.
94. Lygo, B., Allbutt, B., and James, S.R. (2003) Tetrahedron Lett., 44, 5629-5632.
95. Guerin, D.J. and Miller, S.J. (2002) J. Am. Chem. Soc., 124, 2134-2136.
96. Guo, R., Morris, R.H., and Song, D. (2005) J. Am. Chem. Soc., 127, 516-517.
97. Noyori, R., Yamakawa, M., and Hashiguchi, S. (2001) J. Org. Chem., 66, 7931-7944.
98. Källström, S., Jagt, R.B.C., Sillanpää, R., Feringa, B.L., Minnaard, A.J., and Leino, R. (2006) Eur. J. Org. Chem., 3826-3822.
99. Lee, S.J. and Beak, P. (2006) J. Am. Chem. Soc., 128, 2178-2179.
100. Matsuda, T., Shigeno, M., and Murakami, M. (2007) J. Am. Chem. Soc., 129, 12086-12087.