Base-catalyzed Mukaiyama-type aldol additions, a continued quest for stereoselectivity

Tetrahedron Asymmetry

Volumn 24, Issue 21-22, 2013, Pages 1345-1363

  Sutar, Revannath L ^a   Joshi, Navalkishore N ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BASE; CARBONYL DERIVATIVE; LEWIS ACID; LEWIS BASE; SILICON DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; MUKAIYAMA REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

EID: 84887625836     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2013.09.012     Document Type: Review

References (122)

1. For related articles, see S.G. Nelson Tetrahedron: Asymmetry 9 1998 357 389
2. C. Palomo, M. Oiarbide, and J.M. García Chem. Eur. J. 8 2002 36 44
3. D.A. Evans, J.V. Nelson, and T.R. Taber Top. Stereochem. 13 1982 1 115
4. C.H. Heathcock J.D. Morrison, Asymmetric Synthesis Vol. 3 1984 Academic Press New York 111 212
5. L. Xie, K.M. Isenberger, G. Held, and L.M. Dahl J. Org. Chem. 62 1997 7516 7519
6. M. Braun R. Mahrald, Modern Aldol Reactions Vol. 1 2004 Wiley-VCH Weinheim, Germany 1 62
7. P. Arya, and H. Qin Tetrahedron 56 2000 917 947
8. C. Palomo, M. Oiarbide, and J.M. García Chem. Soc. Rev. 33 2004 65 75
9. S.E. Denmark, S.B.D. Winter, X. Su, and K.T. Wong J. Am. Chem. Soc. 118 1996 7404 7407
10. S.E. Denmark, R.A. Stavenger, X. Su, K.-T. Wong, and Y. Nishigaichi Pure Appl. Chem. 70 1998 1469 1476
11. A.G. Myers, and K.L. Widdowson J. Am. Chem. Soc. 114 1992 2765 2767 and references cited therein
12. S. Kobayashi, and K. Nishio J. Org. Chem. 58 1993 2647 2649
13. S.E. Denmark, and B.D. Griedel J. Org. Chem. 59 1994 5136 5138 and references cited therein
14. S.E. Denmark, B.D. Griedel, D.M. Coe, and M.E. Schnute J. Am. Chem. Soc. 116 1994 7026 7043
15. Y. Yamamoto, K. Maruyama, and K. Matsumoto J. Am. Chem. Soc. 105 1983 6963 6965
16. P.L. Creger Tetrahedron Lett. 13 1972 79 82
17. Y. Kita, O. Tamura, F. Itou, H. Yasuda, H. Kishino, Y.Y. Ke, and Y. Tamura J. Org. Chem. 53 1988 554 561
18. M. Anada, T. Washio, Y. Watanabe, and S. Hashimoto Heterocycles 80 2010 1489 1503
19. S.E. Denmark, K.-T. Wong, and R.A. Stavenger J. Am. Chem. Soc. 119 1997 2333 2334
20. Y. Génisson, and L. Gorrichon Tetrahedron Lett. 41 2000 4881 4884
21. T.-P. Loh, L.-C. Feng, and L.-L. Wei Tetrahedron 56 2000 7309 7312 and references cited therein
22. M.D. Rosa, and A. Soriente Tetrahedron 67 2011 5949 5955
23. S.-L. Chen, S.-J. Ji, and T.-P. Loh Tetrahedron Lett. 45 2004 375 377
24. B.W. Gung, Z. Zhu, and R.A. Fouch J. Org. Chem. 60 1995 2860 2864
25. C.T. Wong, and M.W. Wong J. Org. Chem. 70 2005 124 131
26. T. Mukaiyama, K. Narasaka, and K. Banno Chem. Lett. 2 1973 1011 1014
27. S.G. Wierschke, J. Chandrasekhar, and W.L. Jorgensen J. Am. Chem. Soc. 107 1985 1496 1500
28. K. Banno, and T. Mukaiyama Chem. Lett. 4 1975 741 744
29. K. Banno, and T. Mukaiyama Bull. Chem. Soc. Jpn. 49 1976 2284 2291
30. T.K. Hollis, and B. Bosnich J. Am. Chem. Soc. 117 1995 4570 4581
31. H. Hagiwara, H. Inoguchi, M. Fukushima, T. Hoshi, and T. Suzuki Synlett 5 2005 2388 2390
32. E.M. Carreira E.N. Jacobsen, A. Pfaltz, H. Yamamoto, Comprehensive Asymmetric Catalysis I-III Vol. 3 1999 Springer New York 997 1065
33. S. Kobayashi, K. Manabe, H. Ishitani, and J.-I. Matsuo Sci. Synth 4 2002 317 369
34. T. Mukaiyama Angew. Chem., Int. Ed. 43 2004 5590 5614 For reviews see
35. K. Ishihara, and H. Yamamoto R. Mahrwald, Modern Aldol React Vol 2 2004 Wiley-VCH Weinhein, Germany 25 68
36. S.E. Denmark, and G.L. Beutner Angew. Chem., Int. Ed. 47 2008 1560 1638
37. C. Chuit, R.J.P. Corriu, C. Reye, and J.C. Young Chem. Rev. 93 1993 1371 1448
38. V. Gutmann The Donor-Acceptor Approach to Molecular Interactions 1978 Plenum New York
39. V. Gutmann Coord. Chem. Rev. 15 1975 207 237
40. S.E. Denmark, and R.A. Stavenger Acc. Chem. Res. 33 2000 432 440
41. J. Gawronski, N. Wascinska, and J. Gajewy Chem. Rev. 108 2008 5227 5252
42. For reviews see I. Kuwajima, and E. Nakamura Acc. Chem. Res. 18 1985 181 187
43. T. Ooi, and K. Maruoka Acc. Chem. Res. 37 2004 526 533
44. S. Shirakawa, T. Ooi, and K. Maruoka K. Maruoka, Asymmetric Phase Transfer Catalysis 2008 Wiley-VCH Weinhein, Germany 189 206
45. J.-F. Brière, S. Oudeyer, V. Dalla, and V. Levacher Chem. Soc. Rev. 41 2012 1696 1707
46. I. Kuwajima, and E. Nakamura J. Am. Chem. Soc. 97 1975 3257 3258
47. W.A. Kleschick, C.T. Buse, and C.H. Heathcock J. Am. Chem. Soc. 99 1977 247 248
48. R. Noyori, K. Yokoyama, J. Sakata, I. Kuwajima, E. Nakamura, and M. Shimizu J. Am. Chem. Soc. 99 1977 1265 1267
49. R. Noyori, I. Nishida, and J. Sakata J. Am. Chem. Soc. 103 1981 2106 2108
50. E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, and R. Noyori J. Org. Chem. 48 1983 932 945
51. T. Ooi, K. Doda, and K. Maruoka Org. Lett. 3 2001 1273 1276
52. R. Noyori, I. Nishida, and J. Sakata J. Am. Chem. Soc. 105 1983 1598 1608
53. A.R. Bassindale, and T. Stout Tetrahedron Lett. 26 1985 3403 3406
54. S. Matsukawa, N. Okano, and T. Imamoto Tetrahedron Lett. 41 2000 103 107
55. H. Kwart, and K.G. King In d-Orbitals in the Chemistry of Silicon. Phosphorus and Sulfur 1977 Springer Berlin 96 178 Vol. 3
56. S.N. Tandura, M.G. Voronkov, and N.V. Alekseev Top. Curr. Chem. 131 1986 99 189
57. J.I. Musher Angew. Chem. 81 1969 68 83
58. J.I. Musher Angew. Chem., Int. Ed. Engl. 8 1969 54 68
59. O.J. Curnow J. Chem. Educ. 75 1998 910 915
60. M.S. Gordon, M.T. Carroll, L.P. Davis, and L.W. Burggraf J. Phys. Chem. 94 1990 8125 8128
61. M. Kira, K. Sato, H. Sakurai, M. Hada, M. Izawa, and Ushio J. Chem. Lett. 20 1991 387 390
62. S.E. Denmark, and S.B.D. Winter Synlett 1997 1087 1089
63. S.E. Denmark, and R.A. Stavenger J. Org. Chem. 63 1998 918 919
64. S.E. Denmark, K.-T. Wong, R.A. Stavenger, and X. Su J. Am. Chem. Soc. 121 1999 4982 4991
65. S.E. Denmark, and S.M. Pham J. Org. Chem. 68 2003 5045 5055
66. S.E. Denmark, and R.A. Stavenger J. Am. Chem. Soc. 122 2000 8837 8847
67. S.E. Denmark, and S.M. Pham Org. Lett. 3 2001 2201 2204
68. S.E. Denmark, S. Fujimori, and S.M. Pham J. Org. Chem. 70 2005 10823 10840
69. R.A.I.I. Flowers, X. Xu, C. Timmons, and G. Li Eur. J. Org. Chem. 2004 2988 2990
70. S.E. Denmark, B.M. Eklov, P.J. Yao, and M.D. Eastgate J. Am. Chem. Soc. 131 2009 11770 11787 and references cited therein.
71. S.E. Denmark, X. Su, and Y. Nishigaichi J. Am. Chem. Soc. 120 1998 12990 12991
72. S.E. Denmark, R.A. Stavenger, S.B.D. Winter, K.-T. Wong, and P.A. Barsanti J. Org. Chem. 63 1998 9517 9523
73. S.E. Denmark, and S.K. Ghosh Angew. Chem., Int. Ed. 40 2001 4759 4762
74. S.E. Denmark, and T. Bui Proc. Natl. Acad. Sci. U.S.A 101 2004 5439 5444
75. S.E. Denmark, and Y. Fan J. Am. Chem. Soc. 124 2002 4233 4235
76. S.E. Denmark, Y. Fan, and M.D. Eastgate J. Org. Chem. 70 2005 5235 5248
77. M. Nakajima, T. Yokota, M. Saito, and S. Hashimoto Tetrahedron Lett. 45 2004 61 64
78. S. Kotani, S. Hashimoto, and M. Nakajima Synlett 2006 1116 1118
79. M. Nakajima, Y. Orito, T. Ishizuka, and S. Hashimoto Org. Lett. 6 2004 3763 3765
80. Y. Orito, S. Hashimoto, T. Ishizuka, and M. Nakajima Tetrahedron 62 2006 390 400
81. T. Ichibakase, Y. Orito, and M. Nakajima Tetrahedron Lett. 49 2008 4427 4429
82. T. Mukaiyama, H. Fujisawa, and T. Nakagawa Helv. Chim. Acta 85 2002 4518 4531
83. H. Fujisawa, and T. Mukaiyama Chem. Lett. 31 2002 182 183
84. H. Fujisawa, and T. Mukaiyama Chem. Lett. 31 2002 858 859
85. T. Nakagawa, H. Fujisawa, and T. Mukaiyama Chem. Lett. 32 2003 462 463
86. T. Nakagawa, H. Fujisawa, Y. Nagata, and T. Mukaiyama Bull. Chem. Soc. Jpn. 77 2004 1555 1567
87. T. Nakagawa, H. Fujisawa, and T. Mukaiyama Chem. Lett. 32 2003 696 697
88. T. Nakagawa, H. Fujisawa, Y. Nagata, and T. Mukaiyama Bull. Chem. Soc. Jpn. 78 2005 236 246
89. H. Fujisawa, E. Takahashi, and T. Mukaiyama Eur. J. Chem. 12 2006 5082 5093
90. T. Nakagawa, H. Fujisawa, and T. Mukaiyama Chem. Lett. 33 2004 92 93
91. H. Fujisawa, T. Nakagawa, and T. Mukaiyama Adv. Synth. Catal. 346 2004 1241 1246
92. H. Fujisawa, Y. Nagata, Y. Sato, and T. Mukaiyama Chem. Lett. 34 2005 842 843
93. B. Chandra, D. Fu, and S.G. Nelson Angew. Chem., Int. Ed. 49 2010 2591 2594
94. X. Zhang, J. Shi, and S. Hu J. Chem. Res. 5 2010 263 265
95. M. Hatano, E. Takagi, and K. Ishihara Org. Lett. 9 2007 4527 4530
96. M. Hatano, S. Suzuki, E. Takagi, and K. Ishihara Tetrahedron Lett. 50 2009 3171 3174
97. T. Mizugaki, C.E. Hetrick, M. Murata, K. Ebitani, M.D. Amiridis, and K. Kaneda Chem. Lett. 34 2005 420 421
98. G. Mercey, D. Brégeon, C. Baudequin, F. Guillen, J. Levillain, M. Gulea, J.-C. Plaquevent, and A.-C. Gaumont Tetrahedron Lett. 50 2009 7239 7241
99. Z.-L. Shen, S.-J. Ji, and T.-P. Loh Tetrahedron Lett. 46 2005 507 508
100. R. Shrivastav J. Mol. Catal. A: Chem. 264 2007 146 152
101. H. Hagiwara, H. Inoguchi, M. Fukushima, T. Hoshi, and T. Suzuki Tetrahedron Lett. 47 2006 5371 5373
102. X. Zhang, J. Shi, and S. Hu J. Chem. Res. 34 2010 263 265
103. K. Miura, T. Nakagawa, and A. Hosomi J. Am. Chem. Soc. 24 2002 536 537 and references cited therein.
104. J.J. Song, Z. Tan, J.T. Reeves, N.K. Yee, and C.H. Senanayake Org. Lett. 9 2007 1013 1016
105. V.R. Chintareddy, K. Wadhawa, and J.G. Verkade J. Org. Chem. 74 2009 8118 8132
106. S.E. Denmark, T. Wynn, and T. Beutner J. Am. Chem. Soc. 124 2002 13405 13407
107. S.E. Denmark, G.L. Beutner, T. Wynn, and M.D. Eastgate J. Am. Chem. Soc. 127 2005 3774 3789
108. S.E. Denmark, and J.R. Heemstra Jr. Org. Lett. 5 2003 2303 2306
109. S.E. Denmark, and T. Bui J. Org. Chem. 70 2005 10190 10193
110. S.E. Denmark, and W. Chung Angew. Chem., Int. Ed. 47 2008 1890 1892
111. Y. Shimada, T. Tando, S. Kotani, M. Sugiura, and M. Nakajima Tetrahedron: Asymmetry 20 2009 1369 1370
112. M. Sugiura, N. Sato, S. Kotani, and M. Nakajima Chem. Commun. 2008 4309 4311
113. M. Sugiura, N. Sato, Y. Sonoda, S. Kotani, and M. Nakajima Chem.-Asian J. 5 2010 478 481
114. A. Yanagisawa, Y. Nakatsuka, K. Asakawa, H. Kageyama, and H. Yamamoto Synlett 2001 69 72
115. A. Yanagisawa, Y. Nakatsuka, K. Asakawa, M. Wadamoto, H. Kageyama, and H. Yamamoto Bull. Chem. Soc. Jpn. 74 2001 1477 1484
116. M. Ohkouchi, D. Masui, M. Yamaguchi, and Y. Yamagishi J. Mol. Catal. A: Chem. 170 2001 1 16
117. M. Wadamoto, N. Ozasa, A. Yanagisawa, and H. Yamamoto J. Org. Chem. 68 2003 5593 5601
118. S.G. Patel, and S.L. Wiskur Tetrahedron Lett. 50 2009 1164 1166
119. B.K. Senapati, L. Gao, S. Lee, G.-S. Hwang, and D.H. Ryu Org. Lett. 12 2010 5088 5091
120. D.A. Evans, C.W. Downey, and J.L. Hubbs J. Am. Chem. Soc. 125 2003 8706 8707
121. C.W. Dawney, and M.W. Johnson Tetrahedron Lett. 48 2007 3559 3562
122. C.W. Dawney, M.W. Johnson, and K.J. Tracy J. Org. Chem. 73 2008 3299 3302