Lewis base activation of Lewis acids: Catalytic, enantioselective addition of silyl ketene acetals to aldehydes

Journal of the American Chemical Society

Volumn 127, Issue 11, 2005, Pages 3774-3789

  Denmark, Scott E ^a   Beutner, Gregory L ^a   Wynn, Thomas ^a   Eastgate, Martin D ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ADDITION REACTIONS; ALDEHYDES; CATALYSIS; ETHERS; POSITIVE IONS; SILICON;

ENANTIOSELECTIVITY; SILYL CATION COMPLEX; SILYL DIENOL ETHERS; SILYL KETENE ACETALS;

ORGANIC ACIDS;

ACETAL; ALDEHYDE; BENZALDEHYDE; CHLORIDE ION; KETENE DERIVATIVE; LEWIS ACID; LEWIS BASE; SILANE DERIVATIVE; SILICON DERIVATIVE; SILICON TETRACHLORIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 15744387149     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja047339w     Document Type: Article

References (135)

1. Yamamoto, H. Lewis Acids in Organic Synthesis: Wiley-VCH: Weinheim. Germany, 2001.
2. Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC Press: Boca Raton, FL, 1996.
3. Otera, J. Modern Carbonyl Chemistry; Wiley-VCH: Weinheim, Germany, 2000.
4. Schaus, S. E.; Brandes, B. D.; Larrow, J. F.; Tokunaga, M.; Hansen, K. B.; Gould, A. E.; Furrow, M. E.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 1307-1315.
5. Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365-9366.
6. (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323-4326.
7. (b) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570-4581.
8. (a) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; Macmillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893-7894.
9. (b) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392-393.
10. (c) Evans, D. A.; Downey, C. W.; Shaw, J. T.; Tedrow, J. S. Org. Lett. 2002, 4, 1127-1130.
11. (a) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Vol. III, Chapter 29.
12. (b) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-384.
13. (c) Cowden, C. J.; Paterson, I. Org. React. 1997, 51, 1-200.
14. (d) Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-104.
15. (e) Mukaiyama, T. Org. React. 1982, 28, 203-332.
16. (f) Nielsen, A. T.; Houlihan, W. J. Org. React. 1968, 16, 1-438.
17. Berrisford, D. J.; Bolm, C.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1995, 34, 1059-1070.
18. (a) Gutmann, V. The Donor-Acceptor Approach to Molecular Interactions; Plenum Press: New York, 1978.
19. (b) Jensen, W. B. The Lewis Acid-Base Concept; Wiley-Interscience: New York, 1980.
20. (a) Gordon, M. S.; Carroll, M. T.; Davis, L. P.; Burggraf, L. W. J. Phys. Chem. 1990, 94, 8125-8128.
21. (b) Gordon, M. S. Private communication.
22. Kira, M.; Sato, K.; Sakurai, H.; Hada, M.; Izawa, M.; Ushio, J. Chem. Lett. 1991, 387-390.
23. (a) Nelson, S. G.; Wan, Z. Org. Lett. 2000, 2, 1883-1886.
24. (b) Nelson, S. G.; Kim, B.-K.; Peelen, T. J. J. Am. Chem. Soc. 2000, 122, 9318-9319.
25. (c) Evans, D. A.; Johnson, J. S. Org. Lett. 1999, 1, 595-598.
26. (a) Denmark, S. E.; Barsanti, P. A.; Wong, K.-T.; Stavenger, R. A. J. Org. Chem. 1998, 63, 2428-2429.
27. (b) Nakajima, M.; Saito, M.; Uemura, M.; Hashimoto, S. Tetrahedron Lett. 2002, 43, 8827-8829.
28. (c) Tao, B.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 353-354.
29. (a) Hoffman, R. W. Angew. Chem., Int. Ed. 2003, 42, 1096-1109.
30. (b) Jacobsen, E. N.; Wu, M. H. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pflatz, A., Yamamoto, H., Eds.; Springer-Verlag: Heidelberg, Germany, 1999; Vol. III, Chapter 35.1.
31. (a) Denmark, S. E.; Fujimori, S. In Modern Aldol Reactions; Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Chapter 7, p 229.
32. (b) Denmark, S. E.; Stavenger, R. A. Acc. Chem. Res. 2000, 33, 432-440.
33. Denmark, S. E.; Wynn, T. J. Am. Chem. Soc. 2001, 123, 6199-6200.
34. This reaction is mechanistically distinct from those of allyltrichlorosilane: (a) Denmark, S. E.; Fu, J. Chem. Commun. 2003, 167-170.
35. (b) Denmark, S. E.; Fu, J. Org. Lett. 2002, 4, 1951-1953.
36. (c) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2001, 123, 9488-9489.
37. (d) Iseki, K.; Mizuno, S.; Kuroki, Y.; Kobayashi, Y. Tetrahderon 1999, 55, 977-988.
38. (e) Nakajima, M.; Saito, M.; Shiro, M.; Hashimoto, S. J. Am. Chem. Soc. 1998, 120, 6419-6420.
39. (f) Denmark, S. E.; Coe, D. M.; Pratt, N. E.; Griedel, B. D. J. Org. Chem. 1994, 59, 6161-6163.
40. (a) Mayr, H.; Bug, T.; Gotta, M. F.; Hering, N.; Irrang, B.; Janker, B.; Kempf, B.; Loos, R.; Ofial, A. R.; Remennikov, G.; Schimmel, H. J. Am. Chem. Soc. 2001, 123, 9500-9512.
41. (b) Burfeindt, J.; Patz, M.; Müller, M.; Mayr, H. J. Am. Chem. Soc. 1998, 120, 3629-3634.
42. Denmark, S. E.; Winter, S. B. D.; Su, X.; Wong, K.-T. J. Am. Chem. Soc. 1996, 118, 7404-7405.
43. (a) Mukaiyama, T.; Inubushi, A.; Suda, S.; Hara, R.; Kobayashi, S. Chem. Lett. 1990, 1015-1018.
44. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837-8838.
45. (c) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814-5815.
46. (a) Kobayashi, S.; Furuya, M.; Ohtsubo, A.; Mukaiyama, T. Tetrahedron: Asymmetry 1991, 2, 635-638.
47. (b) Kobayashi, S.; Fujishita, Y.; Mukaiyama, T. Chem Lett. 1990, 1455-1458.
48. (a) Masamune, S.; Sato, T.; Kim, B.; Wollman, T. A. J. Am. Chem. Soc. 1986, 108, 8279-8281.
49. (b) Parmee, E. R.; Tempkin, O.; Masamune, S.; Abiko, A. J. Am. Chem. Soc. 1991, 113, 9365-9366.
50. (c) Parmee, E. R.; Hong, Y. P.; Tempkin, O.; Masamune, S. Tetrahedron Lett. 1992, 33, 1729-1732.
51. (a) Mikami, K.; Matsukawa, S.; Sawa, E.; Harada, A.; Koga, N. Tetrahedron Lett. 1997, 38, 1951-1954.
52. (b) Evans, D. A.; MacMillan, D. W. C.; Campos, K. R. J. Am. Chem. Soc. 1997, 119, 10859-10860.
53. (c) Mikami, K.; Matsukawa, S. J. Am. Chem. Soc. 1993, 115, 7039-7040.
54. The zirconium(IV) BINOL system achieves high anti diastereoselectivity with a synthetically useful degree of stereoconvergence for a wide variety of substrates: (a) Yamashita, Y.; Ishitani, H.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 3292-3302.
55. (b) Ishitani, H.; Yamashita, Y.; Shimizu, H.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 5403-5404.
56. Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929-1972.
57. (a) Fleming, I. Frontier Orbitals and Organic Reactions; Wiley-Interscience: New York, 1996.
58. For a notable exception, see: (b) Saito, S.; Nagahara, T.; Shiozawa, M.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6200-6210.
59. For boron, see: (a) Kiyooka, S.-I.; Hena, M. A.; Yabukami, T.; Murai, K.; Goto, F. Tetrahedron Lett. 2000, 41, 7511-7516.
60. (b) Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 839-845.
61. For titanium see: (c) Paterson, I.; Davies, R. D. M.; Heimann, A. C.; Marquez, R.; Meyer, A. Org. Lett. 2003, 5, 4477-4480.
62. (d) DeRosa, M.; Acocella, M. R.; Villano, R.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 2003, 14, 2499-2502.
63. (e) DeRosa, M.; Acocella, M. R.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 2001, 12, 1529-1531.
64. (f) Soriente, A.; DeRosa, M.; Stanzione, M.; Villano, R.; Scettri, A. Tetrahedron: Asymmetry 2001, 12, 959-963.
65. (g) DeRosa, M.; Soriente, A.; Scettri, A. Tetrahedron: Asymmetry 2000, 11, 3187-3195.
66. (h) Szlosek, M.; Figadere, B. Angew. Chem., Int. Ed. 2000, 39, 1799-1801.
67. (i) Soriente, A.; DeRosa, M.; Apicella, A.; Scettri, A.; Sodano, G. Tetrahedron: Asymmetry 1999, 10, 4481-4484.
68. (j) Anne, S.; Yong, W.; Vandewalle, M. Synlett 1999, 1435-1437.
69. (k) Kim, Y.; Singer, R. A.; Camera, E. M. Angew. Chem., Int. Ed. 1998, 37, 1261-1263.
70. (l) Pichon, M.; Jullian, J.-C.; Figadere, B.; Cave, A. Tetrahedron Lett. 1998, 39, 1755-1758.
71. (m) Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Heterocycles 1995, 41, 1435-1444.
72. For copper see: (n) Fettes, A.; Carreira, E. M. Angew. Chem., Int. Ed. 2002, 41, 4098-4101.
73. (o) Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685.
74. (p) Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124-3126.
75. (q) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016.
76. (r) Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838.
77. (s) Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360-12361.
78. For chromium, see: (t) Shimada, Y.; Matsuoka, Y.; Irie, R.; Katsuki, T. Synlett 2004, 57-60.
79. (u) Onitsuka, S.; Matsuoka, Y.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 974-975.
80. (v) Matsuoka, Y.; Irie, R.; Katsuki, T. Chem. Lett. 2003, 32, 584-585.
81. (a) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293-4298.
82. (b) Brennan, C. J.; Campange, J.-M. Tetrahedron Lett. 2001, 42, 5195-5197.
83. (c) Bluet, G.; Bazan-Tajeda, B.; Campange, J.-M. Org. Lett. 2001, 3, 3807-3810.
84. (d) Bluet, G.; Campagne, J.-M. Tetrahedron Lett. 1999, 40, 5507-5509.
85. Portions of this work have been communicated: (a) Denmark, S. E.; Wynn, T.; Beutner, G. L. J. Am. Chem. Soc. 2002, 124, 13405-13407.
86. (b) Denmark, S. E.; Beutner, G. L. J. Am. Chem. Soc. 2003, 125, 7800-7801.
87. Lutz, G. P.; Du, H.; Gallagher, D. J.; Beak, P. J. Org. Chem. 1996, 61, 4542-4554.
88. Van Draanen, N. A.; Arsenivadis, S.; Crimmins, M. T.; Heathcock, C. H. J. Org. Chem. 1991, 56, 2499-2506.
89. Davies, S. G.; Edwards, A. J.; Evans, G. B.; Mortlock, A. A. Tetrahedron 1994, 50, 6621-6642.
90. Kamimura, A.; Mitsudera, H.; Asano, S.; Kidera, S.; Kakehi, A. J. Org. Chem. 1999, 64, 6353-6360.
91. The diastereoselectivity reported in this work for the aldol product derived from 1-naphthaldehyde 5b and 2e (9eb) is higher than that reported in the previous communication. The species originally assigned as the syn diastereomer of 9eb was, in fact, the aldol product derived from 2-naphthaldehyde (9ec). Commercially available 1-naphthaldehyde is contaminated with 2-4% 2-naphthaldehyde (Aldrich). This isomer could not be removed by simple distillation. The observed enantioselectivity is unaffected as the peaks for 9eb and 9ec were well separated in the CSP-SFC analysis.
92. Kobayashi, S.; Ishitani, H.; Yamashita, Y.; Ueno, M.; Shimizu, H. Tetrahedron 2001, 57, 861-866.
93. Herrman, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 14, 2433-2436.
94. Grunwell, J. R.; Karipides, A.; Wigal, C. T.; Heinzman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91-95.
95. 1H NMR analysis.
96. Nuñez, M. T.; Martin, V. S. J. Org. Chem. 1990, 55, 1928-1932.
97. (a) Katsuki, T.; Martin, V. S. Org. React. 1996, 48, 1-300.
98. (b) Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974-5976.
99. Nair, M. S.; Joly, S. Tetrahedron: Asymmetry 2000, 11, 2049-2052.
100. (a) Lokensgard, J. P.; Fisher, J. W.; Bartz, W. J.; Meinwald, J. J. Org. Chem. 1985, 50, 5609-5611.
101. (b) Gundersen, L.-L.; Benneche, T. Acta Chem. Scand. 1991, 45, 975-977.
102. Chloro-1-trichlorosiloxyheptane: Ghosh, S. K. Unpublished results from these laboratories.
103. 2 = 0.798).
104. Kennedy, J. D.; McFarlane, W. In Multinuclear NMR; Mason, J., Ed.; Plenum Press: New York, 1987; Chapter 11, p 305.
105. (a) Bassindale, A. R.; Jiang, J. J. Organomet. Chem. 1993, 446, C3-C5.
106. (b) Swamy, K. C. K.; Chandrasekhar, V.; Harland, J. J.; Holmes, J. M.; Day, R. O.; Holmes, R. R. J. Am. Chem. Soc. 1990, 112, 2341-2348.
107. Kobayashi, S.; Nishio, K. Tetrahedron Lett. 1993, 34, 3453-3456.
108. Karsch, H. H.; Segmueller, T. In Organosilicon Compounds V: From Molecules to Materials; Auner, N., Weis, J., Eds.; Wiley-VCH: Weinheim, Germany, 2003; p 270.
109. Arshadi, M.; Johnels, D.; Edlund, U.; Ottoson, C.-H.; Cremer, D. J. Am. Chem. Soc. 1996, 118, 5120-5131.
110. Marsmann, H. In NMR Basic Principles and Progress, Volume 17; Diehl, P., Fluck, E., Kosfeld, R., Eds.; Springer-Verlag, Berlin, 1981; p 65.
111. Reichardt, C. Solvent and Solvent Effects in Organic Chemistry; Wiley-VCH: Weinheim, Germany, 1988; p 407.
112. 4 by a bispyrrolidine-derived phosphoramide: Schleusner, M. Unpublished results from these laboratories.
113. (a) Denmark, S. E.; Fu, J. J. Am. Chem. Soc. 2003, 125, 2208-2216.
114. (b) Denmark, S. E.; Xu, S. Tetrahedron 1999, 55, 8727-8738.
115. Guthrie, J. P. Can. J. Chem. 1978, 56, 962-973.
116. Sander, E. G.; Jencks, W. P. J. Am. Chem. Soc. 1968, 90, 6154-6162.
117. (a) Granovsky, A. A. (http://classic.chem.msu.su/gran/gamess/index.html).
118. (b) Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jensen, J. H.; Koseki, S.; Matsunaga, N.; Nguyen, K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Montgomery, J. A., Jr. J. Comput. Chem. 1993, 14, 1347-1363.
119. It is reasonable to assume that the aldol reaction occurs through the α-chloro trichlorosilyl ether because products derived from reactions with aliphatic aldehydes give similar levels of selectivity and the same sense of asymmetric induction as that observed with other substrates.
120. Short, J. D.; Attenoux, S.; Berrisford, D. J. Tetrahedron Lett. 1997, 38, 2351-2354.
121. 2EtN may also facilitate catalyst turnover as was seen in the reactions of allyltrichlorosilanes (ref 18).
122. (a) Denmark, S. E.; Heemstra, J. R., Jr. Org. Lett. 2003, 5, 2303-2306.
123. (b) Denmark, S. E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825-7827.
124. Wilcox, C. S.; Babston, R. E. J. Org. Chem. 1984, 49, 1451-1453.
125. Eliel, E. L.; Wilen, S. H.; Mander, L. N. in Stereochemistry of Organic Compounds; John Wiley and Sons: New York, 1994; p 567.
126. Gennari, C.; Bernardi, A.; Cardani, S.; Scolastico, C. Tetrahedron Lett. 1985, 26, 797-800.
127. Kobayashi, S.; Murakami, M.; Mukaiyama, T. Chem. Lett. 1985, 1535-1538.
128. Heathcock, C. H.; Davidsen, S. K.; Hug, K. T.; Flippin, L. A. J. Org. Chem. 1986, 51, 3027-3037.
129. Denmark, S. E.; Lee, W. J. Org. Chem. 1994, 59, 707-709.
130. Tandura, S. N.; Voronkov, M. G.; Alekseev, N. V. Top. Curr. Chem. 1986, 113, 99-189.
131. (a) Jones, G. B. Tetrahedron 2001, 57, 7999-8016.
132. (b) Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885-3896.
133. (c) Hunter, C. A.; Sanders, J. K. M. J. Am. Chem. Soc. 1990, 112, 5525-5534.
134. Although these interactions are known to be weak, especially in nonpolar media, they are enthalpically favorable: Smithrund, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
135. Karabatsos, G. J.; Verdini, A. S. Top. Stereochem. 1970, 5, 167-203.