Reduction of Ketones with LiAlH4 Complexes of α,α,α′,α′-Tetraaryl-1,3-dioxolane-4,5- dimethanols (TADDOLs): A Combination of Enantioselective Reduction and Clathrate Formation with a Discussion of LAH Reagents Bearing C2-Symmetrical Ligands

Croatica Chemica Acta

Volumn 69, Issue 2, 1996, Pages 459-484

  Seebach, Dieter ^a   Beck, Albert K ^a   Dahinden, Robert ^a   Hoffmann, Matthias ^a   Kühnle, Florian N M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001362196     PISSN: 00111643     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (117)

1. Diplomarbeit (Master's Thesis) of R. D., ETH Zürich, 1991/92.
2. Diplomarbeit (Master's Thesis) of M. H., ETH Zürich, 1992/93.
3. Part of the projected Ph. D. Thesis of F. N. M. K., ETH Zürich.
4. Review on Practical and Useful Methods for the Enantioselective Reduction of Unsymmetrical Ketones: V. K. Singh, Synthesis (1992) 605-617.
5. R. Noyori, T. Ohkuma, M. Kitamura, H. Takaya, N. Sayo, H. Kumobayashi, and S. Akutagawa, J. Am. Chem. Soc. 109 (1987) 5856-5858.
6. T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, and R. Noyori, J. Am. Chem. Soc. 117 (1995) 2675-2676.
7. R. Noyori and M. Kitamura, Enantioselective Catalysis with Metal Complexes. An Overview, in: R. Scheffold (Ed.), Modern Synthetic Methods, Vol. 5, Springer, Berlin, Heidelberg, 1989, pp. 115-198.
8. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
9. Review: S. Wallbaum and J. Martens, Tetrahedron Asymm. 3 (1992) 1475-1504.
10. A. Hirao, S. Itsuno, S. Nakahama, and N. Yamazaki, J. Chem. Soc., Chem. Commun. (1981) 315-317.
11. E. J. Corey, R. K Bakshi, and S. Shibata, J. Am. Chem. Soc. 109 (1987) 5551-5552.
12. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem. 107 (1995) 2309-2311; Angew. Chem., Int. Ed. Engl. 34 (1995) 2145-2147.
13. T. Nagata, K. Yorozu, T. Yamada, and T. Mukaiyama, Angew. Chem. 107 (1995) 2309-2311; Angew. Chem., Int. Ed. Engl. 34 (1995) 2145-2147.
14. R. Noyori and M. Kitamura, Angew. Chem. 103 (1991) 34-55; Angew. Chem., Int. Ed. Engl. 30 (1991) 49-69.
15. R. Noyori and M. Kitamura, Angew. Chem. 103 (1991) 34-55; Angew. Chem., Int. Ed. Engl. 30 (1991) 49-69.
16. M. Yoshioka, T. Kawakita, and M. Ohno, Tetrahedron Lett. 30 (1989) 1657-1660.
17. H. Takahashi, T. Kawakita, M. Ohno, M. Yoshioka, and S. Kobayashi, Tetrahedron 48 (1992) 5691-5700.
18. P. Knochel, Synlett (1995) 393-403.
19. Minireview covering the literature up to 1994: R. Dahinden, A. K. Beck, and D. Seebach, α,α,α′,α′-Tetraaryl-2,2-disubstituted-1,3- dioxolane-4,5-dimethanolato-titanium Derivatives (Ti-TADDOLates); in: L. A. Paquette (Ed.), Encyclopedia of Reagents for Organic Synthesis, Vol. 3, Wiley, Chichester, 1995, p.p. 2167-2170.
20. Y. N. Ito, X. Ariza, A. K. Beck, A. Bohác, C. Ganter, R. E. Gawley, F. N. M. Kuhnle, J. Tuleja, Y. M. Wang, and D. Seebach, Helv. Chim. Acta 77 (1994) 2071-2110.
21. A. A. Bothner-By, J. Am. Chem. Soc. 73 (1951) 846.
22. J. D. Morrison and H. S. Mosher, Asymmetric Organic Reactions, Englewood Cliffs, Prentice-Hall, 1970, pp. 160-280.
23. H. Haubenstock, Topics in Stereochemistry 14 (1983) 231-300.
24. 4 Reduction of Ketones, a Comparison of TADDOLates and BINOLates, in: A. F. Abdel-Magid (Ed.), Reduction in Organic Chemistry, ACS Symposium Series, 1996, in press.
25. 4 Reduction of Ketones, a Comparison of TADDOLates and BINOLates, in: A. F. Abdel-Magid (Ed.), Reduction in Organic Chemistry, ACS Symposium Series, 1996, in press.
26. 4 Reduction of Ketones, a Comparison of TADDOLates and BINOLates, in: A. F. Abdel-Magid (Ed.), Reduction in Organic Chemistry, ACS Symposium Series, 1996, in press.
27. H. C. Brown, P. K. Jadhav, and B. Singram, Enantiomerically Pure Compounds via Chiral Organoboranes; in: R. Scheffold (Ed.), Modern Synthetic Methods, Vol. 4, Berlin, Heidelberg, Springer, 1986, pp. 307-356.
28. H. C. Brown and P. V. Ramachandran, Acc. Chem. Res. 25 (1992) 16-24.
29. P. V. Ramachandran, B. Gong, A. V. Teodorovic, and H. C. Brown, Tetrahedron Asymm. 5 (1994) 1061-1074.
30. D. Seebach, A. K. Beck, M. Schiess, L. Widler, and A. Wonnacott, Pure Appl. Chem. 55 (1983) 1807-1822.
31. D. Seebach, B. Weidmann, and L. Widler, Titanium and Zirconium Derivatives in Organic Synthesis; in: R. Scheffold (Ed.), Modern Synthetic Methods, Vol. 3, Sauerländer, Aarau, 1983, pp. 217-353.
32. D. Seebach, A. K. Beck, R. Imwinkelried, S. Roggo, and A. Wonnacott, Helv. Chim. Acta 70 (1987) 954-974.
33. A. K. Beck, B. Bastani, D. A. Plattner, W. Petter, D. Seebach, H. Braunschweiger, P. Gysi, and L. La Vecchia, Chimia 45 (1991) 238-244.
34. A. K. Beck, P. Gysi, L. La Vecchia, and D. Seebach, Org. Syntheses, in preparation.
35. Minireview: G. Kaupp, Angew. Chem. 106 (1994) 768-770; Angew. Chem., Int. Ed. Engl. 33 (1994) 728-729.
36. Minireview: G. Kaupp, Angew. Chem. 106 (1994) 768-770; Angew. Chem., Int. Ed. Engl. 33 (1994) 728-729.
37. E. Weber, N. Dörpinghaus, C. Wimmer, Z. Stein, H. Krupitsky, and I. Goldberg, J. Org. Chem. 57 (1992) 6825-6833.
38. F. Toda, J. Synth. Org. Chem. Jpn. 52 (1994) 923-934.
39. F. Toda, K. Tanaka, and T. Okada, J. Chem. Soc., Chem. Commun. (1995) 639-640.
40. F. Toda, H. Takumi, and K. Tanaka, Tetrahedron Asymm. 6 (1995) 1059-1062.
41. C. von dem Bussche-Hünnefeld, A. K. Beck, U. Lengweiler, and D. Seebach, Helv. Chim. Acta 75 (1992) 438-441.
42. D. Seebach and E. Hungerbühler, Syntheses of Enantiomerically Pure Compounds (EPC-Syntheses). - Tartaric Acid, an Ideal Source of Chiral Building Blocks for Synthesis?, in: R. Scheffold (Ed.), Modern Synthetic Methods, Vol. 2, Salle + Sauerländer, Frankfurt/Aarau, 1980, pp. 91-173.
43. D. Seebach, H.-O. Kalinowski, B. Bastani, G. Crass, H. Daum, H. Dörr, N. P. Du Preez, V. Ehrig, W. Langer, C. Nüssler, H.-A. Oei, and M. Schmidt, Helv. Chim. Acta 60 (1977) 301-325.
44. D. Seebach, H.-A. Oei, and H. Daum, Chem. Ber. 110 (1977) 2316-2333.
45. D. Seebach and W. Langer, Helv. Chim. Acta 62 (1979) 1701-1709.
46. W. Langer and D. Seebach, Helv. Chim. Acta 62 (1979) 1710-1722.
47. D. Seebach, G. Crass, E.-M. Wilka, D. Hilvert, and E. Brunner, Helv. Chim. Acta 62 (1979) 2695-2698; M. Schmidt, R. Amstotz, G. Crass, and D. Seebach, Chem. Ber. 113 (1980) 1691-1707.
48. D. Seebach, G. Crass, E.-M. Wilka, D. Hilvert, and E. Brunner, Helv. Chim. Acta 62 (1979) 2695-2698; M. Schmidt, R. Amstotz, G. Crass, and D. Seebach, Chem. Ber. 113 (1980) 1691-1707.
49. D. Seebach, H.-O. Kalinowski, W. Langer, G. Crass, and E.-M. Wilka, Organic Syntheses 61 (1983) 24-34; Organic Syntheses, Collective Volume VII (1990) 41-50.
50. D. Seebach, H.-O. Kalinowski, W. Langer, G. Crass, and E.-M. Wilka, Organic Syntheses 61 (1983) 24-34; Organic Syntheses, Collective Volume VII (1990) 41-50.
51. D. Seebach and H. Daum, Chem. Ber. 107 (1974) 1748-1763.
52. D. Seebach and H. Meyer, Angew. Chem. 86 (1974) 40-41; Angew. Chem., Int. Ed. Engl. 13 (1974) 77-78.
53. D. Seebach and H. Meyer, Angew. Chem. 86 (1974) 40-41; Angew. Chem., Int. Ed. Engl. 13 (1974) 77-78.
54. H. Meyer and D. Seebach, Liebigs Ann. Chem. (1975) 2261-2278.
55. For a recent application see: E. F. J. de Vries, J. Brussee, C. G. Kruse, and A. van der Gen, Tetrahedron Asymm. 5 (1994) 377-386.
56. O. Cervinka, Coll. Czech. Chem. Commun. 26 (1961) 673-680.
57. S. R. Landor, B. J. Miller, and A. R. Tatchell, J. Chem. Soc. C (1966) 1822-1825.
58. B. Weber and D. Seebach, Tetrahedron 50 (1994) 6117-6128; [Tetrahedron Symposia-in-Print No. 55 on »Mechanistic Aspects of Polar Organometallic Chemistry«].
59. B. Weber and D. Seebach, Tetrahedron 50 (1994) 6117-6128; [Tetrahedron Symposia-in-Print No. 55 on »Mechanistic Aspects of Polar Organometallic Chemistry«].
60. D. Seebach, R. Dahinden, R. E. Marti, A. K. Beck, D. A. Plattner, and F. N. M. Kühnle, J. Org. Chem. 60 (1995) 1788-1799.
61. H. Schäfer and D. Seebach, Tetrahedron 51 (1995) 2305-2324.
62. D. Seebach, E. Devaquet, A. Ernst, M. Hayakawa, F. N. M. Kühnle, W. B. Schweizer, and B. Weber, Helv. Chim. Acta 78 (1995), 1636-1650.
63. D. Seebach, G. Jaeschke, and Y. M. Wang, Angew. Chem. 107 (1995) 2605-2606; Angew. Chem., Int. Ed. Engl. 34 (1995) 2395-2396.
64. D. Seebach, G. Jaeschke, and Y. M. Wang, Angew. Chem. 107 (1995) 2605-2606; Angew. Chem., Int. Ed. Engl. 34 (1995) 2395-2396.
65. E. J. Corey and Y. Matsumura, Tetrahedron Lett. 32 (1991) 6289-6292.
66. A. K. Beck, Unpublished results, ETH Zürich, 1983.
67. We thank Linda v. d. Bussche-Hünnefeld (née Behrendt) for earring out some of these experiments.
68. R. Noyori, I. Tomino, Y. Tanimoto, and M. Nishizawa, J. Am. Chem. Soc. 106 (1984) 6709-6716.
69. R. Noyori, I. Tomino, M. Yamada, and M. Nishizawa, J. Am. Chem. Soc. 106 (1984) 6717-6725.
70. S. Yamaguchi, H. S. Mosher, and A. Pohland, J. Am. Chem. Soc. 94 (1972) 9254-9255.
71. S. Yamaguchi and H. S. Mosher, J. Org. Chem. 38 (1973) 1870-1877.
72. J. A. Marshall, G. S. Welmaker, and B. W. Gung, J. Am. Chem. Soc. 113 (1991) 647-656.
73. See also: J. P. Vigneron and I. Jacquet, Tetrahedron 32 (1976) 939-944.
74. D. Seebach, D. A. Plattner, A. K. Beck, Y. M. Wang, and D. Hunziker, Helv. Chim. Acta 75 (1992) 2171-2209.
75. The minimum of 14 h trituration time is required to achieve an optimum enantiomer enrichment.
76. D. Seebach, Angew. Chem. 100 (1988) 1685-1715; Angew. Chem., Int. Ed. Engl. 27 (1988) 1624-1654.
77. D. Seebach, Angew. Chem. 100 (1988) 1685-1715; Angew. Chem., Int. Ed. Engl. 27 (1988) 1624-1654.
78. E. Weiss, Angew. Chem. 105 (1993) 1565-1587; Angew. Chem., Int. Ed. Engl. 32 (1993) 1501-1523.
79. E. Weiss, Angew. Chem. 105 (1993) 1565-1587; Angew. Chem., Int. Ed. Engl. 32 (1993) 1501-1523.
80. T. Mole and E. A. Jeffery, Organoaluminium Compounds, Elsevier Publishing Company, Amsterdam, 1972.
81. C. Puchot, O. Samuel, E. Duñach, S. Zhao, C. Agami, and H. B. Kagan, J. Am. Chem. Soc. 108 (1986) 2353-2357.
82. D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford, and H. B. Kagan, J. Am. Chem. Soc. 116 (1994) 9430-9439.
83. B. Schmidt and D. Seebach, Angew. Chem. 103 (1991) 1383-1385; Angew. Chem., Int. Ed. Engl. 30 (1991) 1321-1323.
84. B. Schmidt and D. Seebach, Angew. Chem. 103 (1991) 1383-1385; Angew. Chem., Int. Ed. Engl. 30 (1991) 1321-1323.
85. K. Yamamoto, K. Ueno, and K. Naemura, J. Chem. Soc., Perkin Trans. I (1991) 2607-2608.
86. a) H. Suda, S. Kanoh, N. Umeda, M. Ikka, and M. Motoi, Chem. Lett. (1984) 899-902;
87. b) D. Rawson and A. I. Meyers, J. Chem. Soc., Chem. Commun. (1992) 494-496.
88. V. Prelog and G. Helmchen, Angew. Chem. 94 (1982) 614-631; Angew. Chem., Int. Ed. Engl. 21 (1982) 567-583; D. Seebach and V. Prelog, Angew. Chem. 94 (1982) 696-702; Angew. Chem., Int. Ed. Engl. 21 (1982) 654-660.
89. V. Prelog and G. Helmchen, Angew. Chem. 94 (1982) 614-631; Angew. Chem., Int. Ed. Engl. 21 (1982) 567-583; D. Seebach and V. Prelog, Angew. Chem. 94 (1982) 696-702; Angew. Chem., Int. Ed. Engl. 21 (1982) 654-660.
90. V. Prelog and G. Helmchen, Angew. Chem. 94 (1982) 614-631; Angew. Chem., Int. Ed. Engl. 21 (1982) 567-583; D. Seebach and V. Prelog, Angew. Chem. 94 (1982) 696-702; Angew. Chem., Int. Ed. Engl. 21 (1982) 654-660.
91. V. Prelog and G. Helmchen, Angew. Chem. 94 (1982) 614-631; Angew. Chem., Int. Ed. Engl. 21 (1982) 567-583; D. Seebach and V. Prelog, Angew. Chem. 94 (1982) 696-702; Angew. Chem., Int. Ed. Engl. 21 (1982) 654-660.
92. J. A. Nieman, M. Parvez, and B. A. Keay, Tetrahedron Asymm. 4 (1993) 1973-1976.
93. E. Hardegger, E. Maeder, H. M. Semarne, and D. J. Cram, J. Am. Chem. Soc. 81 (1959) 2729-2737.
94. H. Gerlach, Helv. Chim. Acta 51 (1968) 1587-1593.
95. N. Srivastava, A. Mital, and A. Kumar, J. Chem. Soc., Chem. Commun. (1992) 493-494.
96. Meanwhile, Wieser et al. determined the structure of the (+)-5-α-cholestan-3-one acetal of 6 to assign the absolute configuration of 6: J. A. Nieman, B. A. Keay, M. Kubicki, D. Yang, A. Rauk, D. Tsankov, and H. Wieser, J. Org. Chem. 60 (1995) 1918-1919; A. S. C. Chan, C.-C. Lin, J. Sun, W. Hu, Z. Li, W. Pan, A. Mi, Y. Jiang, T.-M. Huang, T.-K. Yang, J.-H. Chen, Y. Wang, and G.-H. Lee, Tetrahedron Asymm. 6 (1995) 2953-2959.
97. Meanwhile, Wieser et al. determined the structure of the (+)-5-α-cholestan-3-one acetal of 6 to assign the absolute configuration of 6: J. A. Nieman, B. A. Keay, M. Kubicki, D. Yang, A. Rauk, D. Tsankov, and H. Wieser, J. Org. Chem. 60 (1995) 1918-1919; A. S. C. Chan, C.-C. Lin, J. Sun, W. Hu, Z. Li, W. Pan, A. Mi, Y. Jiang, T.-M. Huang, T.-K. Yang, J.-H. Chen, Y. Wang, and G.-H. Lee, Tetrahedron Asymm. 6 (1995) 2953-2959.
98. G. Bringmann, M. Gassen, and R. Lardy, Tetrahedron 50 (1994) 10245-10252.
99. L. Claisen, Chem. Ber. 40 (1907) 3903-3914.
100. W. Voss, Liebigs Ann. Chem. 485 (1931) 283-290.
101. N. B. Lorette and W. L. Howard, J. Org. Chem. 25 (1960) 521-525.
102. N. Dörpinghaus Ph. D. Thesis, Rheinische Friedrich-Wilhelms-Universität, Bonn (Germany), 1989.
103. J. Irurre, C. Alonso-Alija, J. F. Piniella, and A. Alvarez-Larena, Tetrahedron Asymm. 3 (1992) 1591-1596.
104. E. Weber, N. Dörpinghaus, and I. Goldberg, J. Chem. Soc., Chem. Commun. (1988) 1566-1568.
105. K. Bowden, I. M. Heilbron, E. R. H. Jones, and B. C. L. Weedon, J. Chem. Soc. (1946) 39-45.
106. D. Fritz, Janssen Chimica Acta 9 (1991) 21-22.
107. R. H. Pickard and J. Kenyon, J. Chem. Soc. 99 (1911) 45-72.
108. R. H. Pickard and J. Kenyon, J. Chem. Soc. 105 (1914) 1115-1131.
109. R. MacLeod, F. J. Welch, and H. S. Mosher, J. Am. Chem. Soc. 82 (1960) 876-880.
110. D. J. Mathre, A. S. Thompson, A. W. Douglas, K. Hoogsteen, J. D. Carroll, E. G. Corley, and E. J. J. Grabowski, J. Org. Chem. 58 (1993) 2880-2888.
111. The absolute configuration of this product is not known but is also assumed to be (S) due to the analogous sense of the optical rotation and the same sequence of the major product enantiomer on the β-CD stationary phase.
112. S. M. Brown, S. G. Davies, and J. A. A. de Sousa, Tetrahedron Asymm. 4 (1993) 813-822.
113. R. Grigg, V. Santhakumar, V. Sridharan, M. Thornton-Pett, and A. W. Bridge, Tetrahedron 49 (1993) 5177-5188.
114. T. Kashiwagi, K. Fujimori, S. Kozuka, and S. Oae, Tetrahedron 26 (1970) 3647-3651.
115. J. B. M. Coppock and F. R. Goss, J. Chem. Soc. (1939) 1789-1792.
116. SHELXS-86, Program for the Solution of Crystal Structures, G. M. Sheldrick, University of Göttingen, 1986.
117. 'SHELXL-93', G. M. Sheldrick, Current Contents, Physical Chemical and Earth Sciences 29 (1989) 14.