Chiral alcohols: Chemical and catalytic methods of preparation by asymmetric reduction;Álcoois quirais: Métodos químicos e catalíticos de obtenção por redução assimétrica

Quimica Nova

Volumn 26, Issue 1, 2003, Pages 112-122

  Temba, Eliane Silvia Codo ^a   de Oliveira, Ione Maria Ferreira ^a   Donnici, Claudio Luis ^a  

^a FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

Asymmetric reduction; Catalysis and electrocatalysis; Chiral alcohols

Indexed keywords

ALCOHOL DERIVATIVE; ALUMINUM DERIVATIVE; ORGANOBORON DERIVATIVE; REAGENT; RHODIUM DERIVATIVE; RUTHENIUM DERIVATIVE;

CATALYSIS; CHEMICAL ANALYSIS; CHIRALITY; ENANTIOMER; MOLECULE; REDUCTION; REVIEW;

EID: 17144474319     PISSN: 01004042     EISSN: None     Source Type: Journal    
DOI: 10.1590/s0100-40422003000100019     Document Type: Review

References (117)

1. Eliel, E.L.; Wilen, S.H.; Mander, L.N.; Stereochemistry of Organic Compounds, John Wiley & Sons Inc.: New York, 1994, cap. 12.
2. Marckwald, W.; Ber. Deutsch. Chem. Ges. 1904, 37, 349 e 1369; Jacques, J.; Bull. Soc. Chim. Fr. 1995, 132, 353.
3. Marckwald, W.; Ber. Deutsch. Chem. Ges. 1904, 37, 349 e 1369; Jacques, J.; Bull. Soc. Chim. Fr. 1995, 132, 353.
4. Pinheiro, S.; Ferreira, V.F.; Quim. Nova 1998, 21, 312.
5. Kagan, H.B. Em Comprehensive Organometallic Chemistry; Wilkinson, G; Stone, G. A., eds.; Pergamon Press: London, 1982, vol. 8, cap. 53.
6. Seebach, D.; Zuger, M.; Helv. Chim. Acta 1982, 65, 495; Sugai, T.; Katoh, O.; Ohta, H.; Tetrahedron 1995, 51, 11987; Mori, K.; Chem. Commun. 1997, 1153.
7. Seebach, D.; Zuger, M.; Helv. Chim. Acta 1982, 65, 495; Sugai, T.; Katoh, O.; Ohta, H.; Tetrahedron 1995, 51, 11987; Mori, K.; Chem. Commun. 1997, 1153.
8. Seebach, D.; Zuger, M.; Helv. Chim. Acta 1982, 65, 495; Sugai, T.; Katoh, O.; Ohta, H.; Tetrahedron 1995, 51, 11987; Mori, K.; Chem. Commun. 1997, 1153.
9. Fráter, G.; Helv. Chim. Acta 1979, 62, 2825; ibid, 1979, 62, 2829.
10. Fráter, G.; Helv. Chim. Acta 1979, 62, 2825; ibid, 1979, 62, 2829.
11. MacLeod, R.; Prosser, H.; Fikentscher, L.; Lanyi, J.; Mosher, H.S.; Biochemistry, 1964, 3, 838; Vesonder, R. F.; Stodola, F. H.; Wickerham, L. J.; Ellis, J. J.; Rohwedder, W. K.; Can. J. Chem. 1971, 49, 2829.
12. MacLeod, R.; Prosser, H.; Fikentscher, L.; Lanyi, J.; Mosher, H.S.; Biochemistry, 1964, 3, 838; Vesonder, R. F.; Stodola, F. H.; Wickerham, L. J.; Ellis, J. J.; Rohwedder, W. K.; Can. J. Chem. 1971, 49, 2829.
13. Prelog, V.; Pure Appl. Chem. 1964, 9, 119; Bestmann, H.-J.; Schobert, R.; Tetrahedron Lett. 1987, 28, 6587.
14. Prelog, V.; Pure Appl. Chem. 1964, 9, 119; Bestmann, H.-J.; Schobert, R.; Tetrahedron Lett. 1987, 28, 6587.
15. Züger, M.F.; Weller, T.; Seebach, D.; Helv. Chim. Acta 1980, 63, 2005.
16. Kramer, A.; Pfander, H.; Helv. Chim. Acta 1982, 65, 293.
17. Ho, Tse-Lok; Enantioselective Synthesis - Natural Products From Chiral Terpenes, John Wiley & Sons, Inc.: New York, 1992.
18. Barrett, A.G.M.; Carr, R.A.E.; Attwood, S.V.; Richardson, G.; Walshe, N.D.A.; J. Org. Chem. 1986, 51, 4840.
19. Tapolczay, D.J.; Thomas, E.J.; Whitehead, J.W.F; Chem. Commun. 1985, 143.
20. Emberger, R.; Hopp, R.; Spec. Chem. 1987, 7, 193.
21. nd ed., American Chemical Society: Washington, 1976.
22. nd ed., American Chemical Society: Washington, 1976.
23. Mori, K.; Tetrahedron 1989, 11, 3233.
24. Takken, W.; Invertebr. Reprod. Dev. 1999, 36, 67.
25. Silva, D. F.; Eiras, A. E.; Vasconcelos, S. D.; International Congress of Entomology, Book-XXI, I, 2000.
26. Noyori, R.; Asymmetric Synthesis of Natural Products, John Wiley & Sons, Inc.: New York, 1994; Singh, V. K.; Synthesis 1992, 605; Noyori, R.; Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, Inc.: New York, 1994.
27. Noyori, R.; Asymmetric Synthesis of Natural Products, John Wiley & Sons, Inc.: New York, 1994; Singh, V. K.; Synthesis 1992, 605; Noyori, R.; Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, Inc.: New York, 1994.
28. Noyori, R.; Asymmetric Synthesis of Natural Products, John Wiley & Sons, Inc.: New York, 1994; Singh, V. K.; Synthesis 1992, 605; Noyori, R.; Asymmetric Catalysis in Organic Synthesis, John Wiley & Sons, Inc.: New York, 1994.
29. Tomioka, K.; Synthesis 1990, 541.
30. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M.; J. Am. Chem. Soc. 1984, 106, 6709.
31. Koshinen, A.; Assymmetric Synthesis of Natural Products, John Wiley & Sons, Londres, 1984; Kanoh, N.; Ishihara, J.; Yamamoto, Y.; Murai A.; Synthesis 2000, 1878.
32. Koshinen, A.; Assymmetric Synthesis of Natural Products, John Wiley & Sons, Londres, 1984; Kanoh, N.; Ishihara, J.; Yamamoto, Y.; Murai A.; Synthesis 2000, 1878.
33. Suzuki, M.; Morita, Y.; Koyano, H.; Koga, M.; Noyori, R.; Tetrahedron 1990, 46, 4809.
34. Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A.; Tetrahedron 2000, 56, 327.
35. Brown, H.C.; Ramachandran, P.V. Em Advances In Asymetric Synthesis; Hassner, A., ed.; JAI Press: London, 1995, vol. 1, p. 147.
36. Brown, H.C.; Ramachandran, P.V.; J. Organomet. Chem. 1995, 500, 1.
37. Brown, H.C.; Mandal, A. K; J. Org. Chem. 1977, 42, 2996; ibid, 1984, 49, 2558.
38. Brown, H.C.; Mandal, A. K; J. Org. Chem. 1977, 42, 2996; ibid, 1984, 49, 2558.
39. Midland, M.M.; Greer, S.; Tramontano, A.; Zderic, S. A.; J. Am. Chem. Soc. 1979, 101, 2352.
40. Midland, M. M.; Tramontano, A.; Kazubski, A.; Graham, R. S.; Tsai, D. J. S.; Cardin, D.B.; Tetrahedron 1984, 40, 1371.
41. Midland, M.M.; McLoughlin, A.; J. Org. Chem. 1984, 49, 1317.
42. Rogic, M.M.; J. Org. Chem. 1996, 61, 1341.
43. Midland, M.M.; Tramontano, A.; Tetrahedron Lett. 1980, 21, 3549.
44. Midland, M.M.; Nguyen, N.H.; J. Org. Chem. 1981, 46, 4107.
45. Johnson, W.S.; Frei, B.; Gopalan, A. S.; J. Org. Chem. 1981, 46, 1512.
46. Brown, H.C.; Chandrasekharan, J.; Ramachandran, P.V.; J. Am. Chem. Soc. 1988, 111, 1539; Brown, H.C.; Chandrasekharan, J.; Ramachandran, P.V.; Heteroat. Chem. 1995, 6, 1.
47. Brown, H.C.; Chandrasekharan, J.; Ramachandran, P.V.; J. Am. Chem. Soc. 1988, 111, 1539; Brown, H.C.; Chandrasekharan, J.; Ramachandran, P.V.; Heteroat. Chem. 1995, 6, 1.
48. Srebnik, M.; Ramachandran, P.V.; Brown, H.C.; J. Org. Chem. 1988, 53, 2916.
49. Brown, H.C.; Chandrasekharan, J.; Ramachandran, P.V.; J. Org. Chem. 1986, 51, 3394.
50. Brown, H.C.; Ramachandran, J.; Weissman, S.A.; Swaminathan, S.; J. Org. Chem. 1990, 55, 6328.
51. Brown, H.C.; Ramachandran, J; Swaminathan, S.; Tetrahedron: Asymmetry 1990, 1, 433.
52. Brown, H.C.; Ramachandran, J; Teodrovic, A.V.; Swaminathan, S.; Tetrahedron Lett. 1991, 32, 6691.
53. Brown, H.C.; Ramachandran, J.; Park, W.S.; Cho, B.T.; J. Org. Chem. 1987, 52, 5406.
54. Itsuno, S.; Ito, K.; Hirao, A.; Nakahama, S.; J. Chem. Soc., Chem. Commun. 1983, 469.
55. Itsuno, S.; Ito, K.; Sakurai, Y.; Hirao, A.; Nakahama, S.; Bull. Chem. Soc. Jpn. 1987, 60, 395.
56. Corey, E.J.; Bakshi, R.K.; Shibata, S.; J. Am. Chem. Soc. 1987, 109, 5551.
57. Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen, C. P.; Sing, V.K.; J. Am. Chem. Soc. 1987, 109, 7925.
58. Cho, B.T.; Chun, Y.S.; Tetrahedron: Asymmetry 1992, 3, 73.
59. Seebach, D.; Angew. Chem., Int. Ed. 1988, 27, 1624.
60. Zassinovich, G.; Mestroni, G.; Gladiali, S.; Chem. Rev 1992, 92, 1051
61. Noyori, R.; Science 1990, 248, 1194.
62. Noyori, R.; Chem. Soc. Rev. 1989, 18, 187.
63. Noyori, R.; Takaya, H.; Acc. Chem. Res. 1990, 23, 345.
64. Noyori, R.; Chemtech 1992, 22, 360.
65. Brunner, H.; Synthesis 1989, 645.
66. Brown, J. M.; Davies, S. G.; Nature 1989, 342, 631.
67. Ojima, I.; Clos, N.; Bastos, C.; Tetrahedron 1989, 45, 6901.
68. Blystone, S.L.; Chem. Rev. 1989, 89, 1663.
69. Morimoto, T.; Takahashi, H.; Achiwa K.; Chem. Pharm. Bull. 1994, 42, 481.
70. Hayashi, T.; Mise, T.; Mitachi, S.; Yamamoto, K; Kumada, M.; Tetrahedron Lett. 1976, 1133.
71. Hayashi, T.; Katsumura, A.; Konishi, M.; Kumada, M.; Tetrahedron Lett. 1979, 425.
72. Tani, K.; Tanigawa, E.; Tatsuno, Y.; Otsuka, S.; Chem. Lett. 1986, 737.
73. Wang, H.; Sakata, T.; Azuma, M.; Ohta, T.; Takaya, H.; Chem. Lett. 1990, 1331.
74. Bakos, J.; Toth, I.; Heil, B.; Marko, L.; J. Organomet. Chem. 1985, 279, 23.
75. Kew, G.; Dearmond, K.; Hanck, K.; J. Phys. Chem. 1974, 78, 727.
76. Botteghi, C.; Caccia, C.; Chelucci, G.; Soccolini, F.; J. Org. Chem. 1984, 49, 4290.
77. Botteghi, C.; Chelucci, G.; Chessa, G.; Delogu, G.; Gladiali, S.; Soccolini, F.; J. Organomet. Chem. 1986, 304, 217.
78. Bolm, C.; Zehnder, M.; Bur, D.; Angew. Chem., Int. Ed. 1990, 29, 205; Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G.; Chem. Ber. 1992, 125, 1169.
79. Bolm, C.; Zehnder, M.; Bur, D.; Angew. Chem., Int. Ed. 1990, 29, 205; Bolm, C.; Ewald, M.; Felder, M.; Schlingloff, G.; Chem. Ber. 1992, 125, 1169.
80. Botteghi, C.; Schionato, A.; Delucchi, O.; Synth. Commun. 1991, 21, 1819.
81. Dholakia, S.; Gillard, R.D.; Wimmer, F.L.; Polyhedron 1985, 4, 791.
82. Nishiyama, H.; Sakaguchi, H.; Nakamura, T.; Horihata, M.; Kondo, M.; Itoh, K.; Organometallics 1989, 8, 846.
83. Nishiyama, H.; Kondo, M.; Nakamura, T.; Itoh, K.; Organometallics 1991, 10, 500.
84. Nishiyama, H.; Yamaguchi, S.; Kondo, M.; Itoh, K.; J. Org. Chem. 1992, 57, 4306.
85. Nishiyama, H., Park, S.B.; Itoh, K.; Tetrahedron: Asymmetry 1992, 3, 1029.
86. Nishiyama, H.; Yamaguchi, S.; Park, S. B.; Itoh, K.; Tetrahedron: Asymmetry. 1993, 4, 143.
87. Brunner, H.; Brandl, P.; J. Organomet. Chem. 1990, 390, C81.
88. Brunner, H.; Brandl, P.; Tetrahedron: Asymmettry 1991, 2, 919.
89. Gladiali, S.; Pinna, L.; Delogu, G.; Graf, E.; Brunner, H.; Tetrahedron: Asymmetry 1990, 1, 931.
90. Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y.; Tetrahedron Lett. 1995, 36, 5239.
91. Mashima, K.; Kusano, K.; Ohta, T.; Noyori, R.; Takaya, H.; J. Chem. Soc. Chem. Commun. 1989, 1208.
92. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R.; J. Am. Chem. Soc. 1988, 110, 629; Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; J. Am. Chem. Soc. 1987, 109, 5856; Kawano, K.; Ishii, Y.; Saburi, M.; Uchida, Y.; J. Chem. Soc. Chem. Commun. 1988, 87; Shao, L.; Kawano, H.; Saburi, S.; Uchida, Y.; Tetrahedron 1993, 49, 1997.
93. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R.; J. Am. Chem. Soc. 1988, 110, 629; Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; J. Am. Chem. Soc. 1987, 109, 5856; Kawano, K.; Ishii, Y.; Saburi, M.; Uchida, Y.; J. Chem. Soc. Chem. Commun. 1988, 87; Shao, L.; Kawano, H.; Saburi, S.; Uchida, Y.; Tetrahedron 1993, 49, 1997.
94. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R.; J. Am. Chem. Soc. 1988, 110, 629; Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; J. Am. Chem. Soc. 1987, 109, 5856; Kawano, K.; Ishii, Y.; Saburi, M.; Uchida, Y.; J. Chem. Soc. Chem. Commun. 1988, 87; Shao, L.; Kawano, H.; Saburi, S.; Uchida, Y.; Tetrahedron 1993, 49, 1997.
95. Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R.; J. Am. Chem. Soc. 1988, 110, 629; Noyori, R.; Ohkuma, T.; Kitamura, M.; Takaya, H.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; J. Am. Chem. Soc. 1987, 109, 5856; Kawano, K.; Ishii, Y.; Saburi, M.; Uchida, Y.; J. Chem. Soc. Chem. Commun. 1988, 87; Shao, L.; Kawano, H.; Saburi, S.; Uchida, Y.; Tetrahedron 1993, 49, 1997.
96. Shao, L.M.; Seki, T.; Kawano, H.; Saburi, M.; Tetrahedron Lett. 1991, 32, 7699.
97. Jones, A. B.; Yamaguchi, M.; Patten, A.; Danishefski, J.; Ragan, J. A.; Smith, D. B.; Schreiber, S. L.; J. Org. Chem. 1989, 54, 17; Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L.; J. Am. Chem. Soc. 1990, 112, 5583.
98. Jones, A. B.; Yamaguchi, M.; Patten, A.; Danishefski, J.; Ragan, J. A.; Smith, D. B.; Schreiber, S. L.; J. Org. Chem. 1989, 54, 17; Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L.; J. Am. Chem. Soc. 1990, 112, 5583.
99. Schreiber, S. L.; Kelly, S.E.; Porco, J. A.; Sammakia, T.; Suh, E. M.; J. Am. Chem. Soc. 1988, 110, 6210.
100. Taber, D.F.; Deker, P.B.; Silverberg, L.J.; J. Org. Chem. 1992, 57, 5990.
101. Tallec, A.; Bull. Soc. Chim. Fr. 1984, 743.
102. Oliveira, I. M. F.; Moutet, J.-C.; J. Mol. Catal. 1993, 81, L19.
103. Oliveira, I. M. F.; Moutet, J.-C.; J. Electroanal. Chem. 1993, 361, 203.
104. Bettega, H. C.-Y.; Moutet, J.-C.; J. Electroanal. Chem. 1994, 364, 271.
105. Chardon-Noblat, S.; Oliveira, I. M. F.; Moutet, J.-C., Tingry, S.; J. Mol. Catal. A: Chem. 1995, 13.
106. Bettega, H.C.; Moutet, J.-C., J. Electroanal. Chem. 1994, 364, 271.
107. Oliveira, I. M. F.; Moutet, J.-C.; Vlachopoulos, N.; J. Electroanal. Chem. 1990, 291, 243.
108. Schnyder, A.; Togni, A.; Wiesli, U.; Organometallics 1997, 16, 255.
109. Kariv, E.; Terni, H. A.; Gileadi, E.; J. Electrochem. Soc. 1990, 120, 639; Horner, L. Em Organic Electrochemistry; Lund, H.; Baizer, M. M., eds.; Marcel Dekker: New York, 2 ed., 1983, p. 945.
110. Kariv, E.; Terni, H. A.; Gileadi, E.; J. Electrochem. Soc. 1990, 120, 639; Horner, L. Em Organic Electrochemistry; Lund, H.; Baizer, M. M., eds.; Marcel Dekker: New York, 2 ed., 1983, p. 945.
111. Seebach, D.; An Oei, H.; Angew. Chim., Int. Ed. 1975, 14, 634.
112. Gourley, R. N.; Grimshaw, J.; Millard, P. G.; J. Chem. Soc. C 1970, 2318; Kopilov, J.; Kariv, E.; Miller, L. L.; J. Am. Chem. Soc. 1977, 99, 3450; Hazard, R.; Jaouannet, S.; Tallec, A.; Tetrahedron 1982, 38, 93.
113. Gourley, R. N.; Grimshaw, J.; Millard, P. G.; J. Chem. Soc. C 1970, 2318; Kopilov, J.; Kariv, E.; Miller, L. L.; J. Am. Chem. Soc. 1977, 99, 3450; Hazard, R.; Jaouannet, S.; Tallec, A.; Tetrahedron 1982, 38, 93.
114. Gourley, R. N.; Grimshaw, J.; Millard, P. G.; J. Chem. Soc. C 1970, 2318; Kopilov, J.; Kariv, E.; Miller, L. L.; J. Am. Chem. Soc. 1977, 99, 3450; Hazard, R.; Jaouannet, S.; Tallec, A.; Tetrahedron 1982, 38, 93.
115. Watkins, B. F.; Behling, J. R.; Kariv, E.; Miller, L. L.; J. Am. Chem. Soc. 1975, 97, 3549.
116. Fujihira, M.; Yokosawa, A.; Kinoshita, H.; Osa, T.; Chem. Lett. 1982, 1089.
117. Moutet, J.-C.; Cho, L.Y.; Duboc-Toia, C.; Ménage, S.; Riesgo, E. C.; Thummel, R. P.; New J. Chem. 1999, 23, 939.