Stereoselective aldol additions of achiral ethyl ketone-derived trichlorosilyl enolates

Journal of Organic Chemistry

Volumn 68, Issue 13, 2003, Pages 5045-5055

  Denmark, Scott E ^a   Pham, Son M ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STEREOSELECTIVITIES;

ADDITION REACTIONS; ALDEHYDES; STEREOCHEMISTRY;

KETONES;

ALDEHYDE; AMIDE; KETONE; PHOSPHOROAMIDE; SILANE DERIVATIVE; TRICHLOROSILANE DERIVATIVE; TRICHLOROSILYL ENOLATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; DIASTEREOISOMER; ENANTIOSELECTIVITY; GEOMETRY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038548527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034092x     Document Type: Article

References (92)

1. Norcross, R. D.; Paterson, I. Chem. Rev. 1995, 95, 2041.
2. (a) Carreira, E. M. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinhiem, Germany, 2000; Chapter 8.
3. (b) Palomo, C.; Oiarbide, M.; Garcfa, J. M. Chem. Eur. J. 2002, 8, 37.
4. (c) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
5. (d) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Vol. III, Chapter 29.
6. (e) Saito, S.; Yamamoto, H. Chem. Eur. J. 1999, 5, 1959.
7. (f) Nelson, S. G. Tetrahedron: Asymmetry 1998, 357.
8. (g) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137.
9. (h) Paterson, I.; Cowden, C. J.; Wallace, D. J. In Modern Carbonyl Chemistry; Otera, J., Ed.; Wiley-VCH: Weinheim, Germany, 2000; Chapter 9.
10. (i) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1.
11. (j) Heathcock, C. H.; Kim, B. M.; Williams, S. F.; Masamune, S.; Paterson, I.; Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 2.
12. (a) Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S. Angew. Chem., Int. Ed. 2000, 112, 46.
13. (b) Mukaiyama, T. Tetrahedron 1999, 55, 8609.
14. For examples of chiral auxiliaries see: (a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127.
15. (b) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudary, K. J. Org. Chem. 2001, 66, 894.
16. (c) Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
17. (d) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586.
18. For examples of chiral metalloids see: (e) Evans, D. A.; Rieger, D. L.; Bilodeau, M. T.; Urpí, F. J. Am. Chem. Soc. 1991, 113, 1047.
19. (f) Duthaler, R. O.; Hafner, A. Chem. Rev. 1992, 92, 807.
20. (g) Roos, G. H. P.; Haines, R. J.; Raab, C. E. Synth. Commun. 1993, 23, 1251.
21. (h) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
22. (i) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976.
23. (j) Fujimura, O. J. Am. Chem. Soc. 1998, 120, 10032.
24. (k) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
25. (l) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
26. (m) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
27. For examples of chiral Lewis acids, see: (n) Kiyooka, S.-I. Rev. Heteroat. Chem. 1997, 17, 245.
28. (o) Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365.
29. (p) Furata, K.; Maruyama, T.; Yamamoto, H. J. Am. Chem. Soc. 1991, 113, 1041.
30. (q) Ishimaru, K.; Monda, K.; Yamamoto, H.; Akiba, K.-Y. Tetrahedron 1998, 54, 727.
31. (r) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
32. (s) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360.
33. (t) Kim, Y.; Singer, R. A.; Carreira, E. M. Angew. Chem.,Int. Ed. 1998, 37, 1261.
34. (u) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
35. (v) Kobayashi, S.; Nagayama, S.; Busujima, T. Tetrahedron 1999, 55, 8739.
36. (w) Yanagisawa, A.; Matsumoto, Y.; Nakashima, H.; Asakawa, K.; Yamamoto, H. J. Am. Chem. Soc. 1997, 119, 9319.
37. (x) Yamashita, Y.; Saito, S.; Ishitani, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292.
38. (y) Ishitani, H.; Yamashita, Y.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 5403.
39. (a) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168.
40. (b) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
41. (c) Yamada, Y. M. A.; Shibasaki, M. Tetrahedron Lett. 1998, 39, 5561.
42. (d) List, B.; Lerner, R. A.; Barbas, C. F., III J. Am. Chem. Soc. 2000, 122, 2395.
43. (e) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III J. Am. Chem. Soc. 2001, 123, 5260.
44. (f) Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
45. (g) Trost, B. M.; Ito, H. J. Am. Chem. Soc. 2000, 122, 12993.
46. (h) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett, 2001, 3, 2497.
47. (i) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367.
48. (a) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432.
49. (b) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4928.
50. (c) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333.
51. (d) Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404.
52. (a) Denmark, S. E.; Stavenger, R. A. J. Am. Chem. Soc. 2000, 122, 8837.
53. (b) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T. J. Org. Chem. 1998, 63, 918.
54. (a) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982.
55. (b) Denmark, S. E.; Stavenger, R. A.; Winter, S. B. D.; Wong, K.-T.; Barsanti, P. A. J. Org. Chem. 1998, 63, 9517.
56. Hall, P. L.; Gilchrist, J. H.; Collum, D. B. J. Am. Chem. Soc. 1991, 113, 9571.
57. Evans, D. A.; Nelson, J. V.; Vogel, E.; Taber, T. R. J. Am. Chem. Soc. 1981, 103, 3099.
58. Mukaiyama, T.; Inoue, T. Bull Chem. Soc. Jpn. 1980, 53, 174.
59. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324.
60. Denmark, S. E.; Ghosh, S. K. Angew. Chem., Int. Ed. 2001, 40, 4759.
61. Vedejs, E.; Larsen, S. D. J. Am. Chem. Soc. 1984, 106, 3030.
62. (a) Denmark, S. E.; Pham, S. M. Helv. Chim. Acta 2000, 53, 1846.
63. (b) Denmark, S. E.; Su, X.; Nishigaichi, Y. J. Am. Chem. Soc. 1998, 120, 12990.
64. (a) Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951.
65. (b) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488.
66. (c) Denmark, S. E.; Wynn, T. A. J. Am. Chem. Soc. 2001, 123, 6199.
67. Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2002, 124, 4233.
68. House, H. O.; Auerbach, R. A.; Gall, M.; Peet, N. P. J. Org. Chem. 1973, 38, 514.
69. Yamamoto, Y.; Maruyama, K. J. Am. Chem. Soc. 1982, 104, 2323.
70. Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
71. (a) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
72. (a) Bluthe, N.; Malacria, M.; Gore, J. Tetrahedron 1984, 40, 3277. Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
73. (b) Drouin, J.; Boaventura, M.-A.; Conia, J.-M. J. Am. Chem. Soc. 1985, 107, 1726.
74. For a discussion of steric effects in organic chemistry as well as a listing of Taft steric parameters, see: Newman, M. S., Ed. Steric Effects in Organic Chemistry; Wiley: New York, 1956.
75. (a) Miller, R. D.; McKean, D. R. Synthesis 1979, 730.
76. (b) Cazeau, P.; Buboudin, F.; Moulines, F.; Babot, O.; Dunogues, J. Tetrahedron 1987, 43, 2075.
77. (c) Fataftah, Z. A.; Ibrahm, M. R.; Abdel-Rahman, H. N. Bull. Chem. Soc. Jpn. 1991, 64, 671.
78. (a) Goetz, R. W.; Orchin, M. J. Am. Chem. Soc. 1963, 85, 2783.
79. (b) Prince, R. H.; Raspin, K. A. J. Chem. Soc. (A) 1969, 612.
80. (c) Noyori, R.; Umeda, I.; Ishigami, T. J. Org. Chem. 1972, 37, 1542.
81. (d) Bennett, M. A.; Watt, R. Chem. Commun. 1971, 95.
82. (e) Yoshimura, N.; Murahashi, S.-I.; Moritani, I. J. Organomet. Chem. 1973, 52, C58.
83. (a) Fujii, A.; Hagiwara, E.; Sodeoka, M. J. Am. Chem. Soc. 1999, 121, 5450.
84. (b) Sodeoka, M.; Tokunoh, R.; Miyazaki, F.; Hagiwara, E.; Shibasaki, M. Synlett 1997, 463.
85. (a) Sodeoka, M.; Ohrai, K.; Shibasaki, M. J. Org. Chem. 1995, 60, 2648.
86. (b) Albéniz, A. C.; Catalina, N. M.; Espinet, P.; Redón, R. Organometallics 1999, 18, 5571.
87. (c) Nokami, J.; Mandai, T.; Watanabe, H.; Ohyama, H.; Tsuji, J. J. Am. Chem. Soc. 1989, 111, 4126.
88. (d) Ito, Y.; Aoyama, H.; Hirao, T.; Mochizuki, A.; Saegusa, T. J. Am. Chem. Soc. 1979, 101, 494.
89. Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
90. 4 complex (ref 29), and (3) the expected activating effect of a stronly donating phosphoramide ligand trans to the enolate (ref 30).
91. Denmark, S. E.; Su, X. Tetrahedron 1999, 55, 8727.
92. Coe, B. J.; Glenwright, S. J. Coord. Chem Rev. 2000, 203, 5.