The Aldol-Tishchenko reaction: A tool in stereoselective synthesis

Current Organic Chemistry

Volumn 7, Issue 17, 2003, Pages 1713-1723

  Mahrwald, Rainer ^a  

^a HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ENANTIOSELECTIVITY; KETONES; STEREOSELECTIVITY;

ALDOL-TISHCHENKO REACTION; DIASTEREOSELECTIVE REDUCTION; DIMERIZATIONS; MONOESTERS; NATURAL PRODUCT SYNTHESIS; OXIDATION REDUCTION; REDUCTION SEQUENCE; STEREOSELECTIVE SYNTHESIS; TRIMERIZATION;

ALDEHYDES;

ALDEHYDE; ESTER; KETOL;

ADDITION REACTION; ALDOL REACTION; ALDOL TISHCHENKO REACTION; ASYMMETRIC SYNTHESIS; CANNIZZARO REACTION; CHEMICAL MODIFICATION; DIASTEREOISOMER; DIMERIZATION; ENANTIOSELECTIVITY; INTERMETHOD COMPARISON; LITERATURE; OXIDATION REDUCTION REACTION; REDUCTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS; TISHCHENKO REACTION;

EID: 0141920762     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272033486224     Document Type: Review

References (105)

1. Tishchenko, W. Chem. Zentralbl. 1906, 77, 1309;
2. Tishchenko, W. Chem. Zentralbl. 1906, 77, 1552.
3. (a) Saegusa, T.; Kitagawa, S.; Ueshima, T. Bull. Chem. Soc. Jpn. 1967, 40, 1960.
4. (b) Saegusa, T.; Ueshima, T.; Kitagawa, S. Bull. Chem. Soc. Jpn. 1969, 42, 248.
5. Ogata, Y.; Kawasaki, A. Tetrahedron, 1969, 25, 929.
6. Ogata, Y.; Kawasaki, A. Tetrahedron, 1969, 25, 2845.
7. Stapp, P. R. J. Org. Chem. 1973, 38, 1433.
8. Tsuda, T.; Habu, H.; Saegusa, T. J. Chem. Soc., Chem. Comm. 1974, 620.
9. Collin, J.; Namy, J.-L.; Kagan, H. B. Nouv. J. Chim. 1986, 10, 229.
10. Yamaguchi, I.; Kimishima, T.; Osakada, K.; Yamamoto, T. J. Polym. Science Part A: Polym. Chem. 1997, 35, 2821;
11. Yamaguchi, I.; Kimishima, T.; Osakada, K.; Yamamoto, T. J. Polym. Science Part A: Polym. Chem. 1997, 35, 1265.
12. Bunce, R. A.; Shellhammer, A. J. Org. Prep. and Procedures 1987, 19, 161.
13. Bernhard, K. A.; Atwood, J. D. Organometallics 1988, 7, 235;
14. Bernhard, K. A.; Atwood, J. D. Organometallics 1989, 8, 795.
15. Kondo, T.; Akazome, M.; Tsuji, Y.; Watanbe, Y. J. Org. Chem. 1990, 55, 1286.
16. Slough, G.A.; Ashbaugh, J.R.; Zannoni, L.A. Organometallics 1994, 13.
17. Ozawa, F.; Yamagami, I.; Yamamoto, A. J. Organomet. Chem. 1994, 473, 265.
18. Morita, K.-I.; Nishiyama, Y.; Ishii, Y. Organometallics, 1993, 12, 3748.
19. Washington, J.; McDonald, R.; Takats, J.; Menashe, N.; Reshef, D.; Shvo, Y. Organometallics 1995; 14, 3996.
20. Onozawa, S.-Y.; Sakakura, T.; Tanaka, M.; Shiro, M. Tetrahedron, 1996, 52, 4291.
21. Choi, S.-H.; Yashima, E.; Okamoto, Y. Polymer J. 1997, 29, 261.
22. (a) Berberich, H.; Roesky, P. W. Angew. Chem. 1998, 110, 1618,
23. Angew. Chem., Int. Ed. Engl. 1998, 37, 1569.
24. b) Bürgstein, M. R.; Berberich, H.; Roesky, P. W. Chem. Eur. J. 2001, 7, 3078.
25. (a) Ooi, T.; Miura, T.; Takaya, K.; Maruoka, K. Tetrahedron Lett. 1999, 40, 7695.
26. b) Maruoka, K. Catal. Today 2001, 66, 33
27. Ooi, T.; Miura, T.; Itagaki, Y.; Ichikawa, H.; Maruoka, K. Synthesis 2002, 279.
28. Le Bideau, F.; Coradin, T.; Gourier, D.; Henique, J.; Samuel, E. Tetrahedron Lett. 2000, 41, 5215.
29. Deacon, G. B.; Gitlits, A.; Roesky, P. W.; Bürgstein, M. R.; Lim, K. C.; Skelton, B. W.; White, A. H. Chem. Eur. J. 2001, 7, 127.
30. (a) Törmäkangas, O. P.; Koskinen, A. M. Org. Process Res. Dev. 2001, 5, 421.
31. (b) Törmäkangas, O. P.; Koskinen, A. M. Tetrahedron Lett. 2001, 42, 2743.
32. Simpura, I.; Nevalainen, V. Tetrahedron 2001, 57, 9867.
33. Maslinska-Solich, J.; Rudnicka, I.; Jedlinski, Z. J. J. Chem. Soc., Perkin Trans 1, 1981, 3035.
34. Choi, S.-H.; Yashima, E.; Okamoto, Y. Macromolecules, 1996, 29, 1880.
35. Paquette, L. A.; Ohmori, N.; Lowinger, T. B.; Rogers, R. D. J. Org. Chem. 2000; 65, 4303
36. Uenishi, J.'I.; Masuda, S.; Wakabayashi, S. Tetrahedron Lett. 1991, 32, 5097.
37. Lange, G. L.; Organ, M. G. Synlett 1991, 665.
38. Chuang, T.-H.; Fang, J.-M.; Jiaang, W.-T.; Tsai, Y.-M. J. Org. Chem. 1996, 61, 1794.
39. Adinolfi, M.; Barone, G.; De Lorenzo, F.; Iadonisi, A. Synlett, 1999, 336.
40. Hsu, J.-L.; Fang, J.-M. J. Org. Chem. 2001; 66, 8573.
41. Grushin, V. V.; Alper, H. J. Org. Chem. 1991, 56, 5159.
42. Zuchi, C.; Soos, E.; Galamb, V.; Varadi, G.; Parkany, L.; Palyi, G. Eur. J. Inorg. Chem. 2001, 9, 2207.
43. Choi, S.-H.; Yashima, E.; Okamoto, Y. Polym. J. 1997, 29, 261.
44. Yamaguchi, I.; Kimishima, T.; Osakada, K.; Yamamoto, T. J. Polym. Sci. Part A: Polym. Chem. 1997, 35, 2821.
45. Yamaguchi, I.; Kimishima, T.; Osakada, K.; Yamamoto, T. J. Polym. Sci. Part A: Polym. Chem. 1997, 35, 1265.
46. Tanabe, K.; Saito, K. J. Catal. 1974, 35, 247.
47. Tsujii, H.; Yagi, F.; Hattori, H.; Kita, H. J. Catal. 1994, 148, 759.
48. (a) Idriss, H.; Seebauer, E. G. J. Mol. Catal. A: 2000, 152, 201.
49. (b) Idriss, H.; Seebauer, E. G. Catal. Lett. 2000, 66, 139.
50. Kabashima, H.; Tsujii, H.; Nakata, S.; Tanaka, Y.; Hattori, H. Appl. Catal. A: 2000, 194-195, 227.
51. Seki, T.; Akutsu, K.; Hattori, H. Chem. Comm. 2001, 1000.
52. Arammendia, M. A.; Borau, V.; Jimenez, C.; Marinas, J. M.; Ruiz, J. R.; Urbano, F. J. J. Colloid Interface Sci. 2001, 238, 385.
53. Seki, T.; Hattori, H. J. Chem. Soc., Chem. Comm. 2001, 2510.
54. Seki, T.; Kabashima, H.; Akutsu, K.; Tachikawa, H.; Hattori, H. J. Catal. 2001, 204, 393.
55. Hattori, H. Appl. Catal. A: General 2001, 222, 247.
56. (a) Franke, A.; Kohn, L. Monatsh. Chem. 1889, 19, 354.
57. b) Neustädter, V. Monatsh. Chem. 1906, 27, 879.
58. c) Morgenstern, M. Monatsh. Chem. 1903, 24, 579.
59. d) Kirschbaum, M.A. Monatsh. Chem. 1904, 25, 249.
60. For a review see: Peterson, J.; Timotheus, H.; Maeorg, U. Proc. Estonian Acad. Sci. Chem. 1997, 46, 93.
61. (a) Casnati, G.; Pochini, A.; Salerno, G.; Ungaro, R. Tetrahedron Lett. 1974, 12, 959.
62. b) Pochini, A.; Salerno, G.; Ungaro, R. Synthesis 1975, 164.
63. (c) Casnati, G.; Pochini, A.; Salerno, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. I, 1975, 1527.
64. Miyano, A.; Tashiro, D.; Kawasaki, Y.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 6901.
65. Lu, L.; Chang, H.-Y.; Fang, J.-M. J. Org. Chem. 1999, 64, 843.
66. Mascarenhas, C.M.; Duffey, M.O.; Liu, S.-Y.; Morken, J.P. Org. Lett. 1999, 1, 1427.
67. Loog, O.; Maeorg, U. Tetrahedron: Asymmetry 1999, 10, 2411.
68. Mascarenhas, C.M.; Miller, S.P.; White, P.S.; Morken, J.P. Angew. Chem. 2001, 113, 621,
69. Angew. Chem., Int. Ed. Engl. 2001, 40, 601.
70. Fouquet, G.; Merger, F.; Platz, R. Liebigs Ann. Chem. 1979, 1591.
71. a) Trost, B. Science 1991, 254, 1471.
72. b) Trost, B.M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
73. Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30.
74. Curran, D. P.; Wolin, R. L. Synlett 1991, 317.
75. Horiuchi, Y.; Taniguchi, M.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1995, 36, 5353
76. Mahrwald, R.; Costisella, B. Synthesis 1996, 1087.
77. Baramee, A.; Chaichit, N.; Intawee, P.; Thebtaranonth, C.; Thebtaranonth, Y. J. Chem. Soc., Chem. Comm. 1991, 1016.
78. Bodnar, P. M.; Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 5674.
79. Abu-Hasanayan, F.; Streitweiser, A. J. Org. Chem. 1998, 63, 2954.
80. Delas, C.; Blacque, O.; Moise, C. J. Chem. Soc., Perkin Trans. 1 2000, 2265.
81. Shotwell, J. B.; Krygowski, E. S.; Hines, J.; Koh, B.; Huntsman, E. W. D.; Choi, H. W.; Schneekloth, J. S.; Wood, J. L.; Crews, C. M. Org. Lett. 2002, 4, 3087.
82. Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
83. Romo, D.; Meyer, S. D.; Johnson, D. D.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 7906.
84. Wild, R.; Schmidt, R. R. Tetrahedron: Asymmetry 1994, 5, 2195.
85. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 47, 8245.
86. Schöning, K.-U.; Hayashi, R.K.; Powell, D.R. Kirschning, A. Tetrahedron: Asymmetry 1999, 10, 817.
87. Paterson, I.; Davies, R.D.M.; Marquez, R. Angew. Chem. 2001, 113, 623.
88. Paterson, I.; Davies, R.D.M.; Marquez, R. Angew. Chem., Int. Ed. Engl. 2001, 40, 603.
89. Paterson, I.; Florence, G. D.; Gelach, K.; Scott, J. P.; Sereinig, N. J. Am. Chem. Soc. 2001, 123, 9535.
90. Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463.
91. Iwamoto, K.; Chatani, N.; Murai, S. J. Organomet. Chem. 1999, 574, 171.
92. Umekawa, Y.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1997, 62, 3409.
93. Gillespie, K. M.; Munslow, I. J.; Scott, P. Tetrahedron Lett. 1999, 40, 9371.
94. Mellor, J. M.; Reid, G.; El-Sagheer, A. H.; El-Tamany, E. S. H. Tetrahedron 2000, 56, 10039.
95. Schneider, C.; Hansch, M. Chem. Comm. 2001, 1218.
96. Enders, D.; Ince, S. J.; Bonnekessel, M.; Runsink, J.; Raabe, G. Synlett, 2002, 962.
97. Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. Angew. Chem. 1998, 110, 2526;
98. Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. Angew. Chem. Int. Ed. Engl. 1998, 37, 2354.
99. Smith, A. B. III; Lee, D.; Adams, C. M.; Kozlowski, M. C. Org. Lett. 2002, 4, 4539;
100. Smith, A. B. III; Adams, C. M.; Barbosa, S. A. L.; Degnan, A. P. J. Am. Chem. Soc. 2003, 125, 350.
101. Takeno, M.; Kikuchi, S.; Morita, K.-I.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1995, 60, 4974.
102. Fan, C.-A.; Wang, B.-M.; Tu, Y.-Q.; Song, Z.-L. Angew. Chem. 2001, 113, 3995
103. Fan, C.-A.; Wang, B.-M.; Tu, Y.-Q.; Song, Z.-L. Angew. Chem., Int. Ed. Engl. 2001, 40, 3877.
104. Tu, Y.-Q.; Sun, L. D.; Wang, P. Z. J. Org. Chem. 1999, 64, 629.
105. Kodama, T.; Shuto, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2002, 67, 7706.