Asymmetric Mukaiyama aldol reactions using chiral diamine-coordinated Sn (II) triflate: Development and application to natural product synthesis

Chemical Record

Volumn 14, Issue 1, 2014, Pages 144-183

  Shiina, Isamu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

asymmetric synthesis; chiral diamines; ketene silyl acetals; Mukaiyama aldol reaction; tin

Indexed keywords

3-HYDROXYBUTANAL; ALDEHYDE; ALDOL; BIOLOGICAL PRODUCT; COORDINATION COMPOUND; DIAMINE; MESYLIC ACID DERIVATIVE; PROLINE; TIN; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; BIOLOGICAL PRODUCTS; CATALYSIS; COORDINATION COMPLEXES; DIAMINES; MESYLATES; PROLINE; STEREOISOMERISM; TIN;

EID: 84894852770     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201300022     Document Type: Conference Paper

References (119)

1. a) T. Mukaiyama, K. Narasaka, K. Banno, Chem. Lett. 1973, 2, 1011
2. b) T. Mukaiyama, K. Banno, K. Narasaka, J. Am. Chem. Soc. 1974, 96, 7503
3. c) K. Saigo, M. Osaki, T. Mukaiyama, Chem. Lett. 1975, 4, 989
4. d) T. Mukaiyama, Org. React. 1982, 28, 203
5. e) T. Mukaiyama, K. Narasaka, Org. Synth. 1987, 65, 6.
6. For recent reviews of the Mukaiyama aldol reaction, see: a), G. L. Beutner, S. E. Denmark, Angew. Chem., Int. Ed. 2013, 52, 9086
7. b) S. B. J. Kan, K. K.-H. Ng, I. Paterson, Angew. Chem., Int. Ed. 2013, 52, 9097
8. c) J. Matsuo, M. Murakami, Angew. Chem., Int. Ed. 2013, 52, 9109.
9. For reviews of synthetic applications using ESEs and KSAs, see: a), J. K. Rasmussen, Synthesis 1977, 91
10. b) P. Brownbridge, Synthesis 1983, 1
11. c) P. Brownbridge, Synthesis 1983, 85.
12. A. Wissner, Synthesis 1979, 27.
13. a) L. Lozzi, A. Ricci, M. Taddei, J. Org. Chem. 1984, 49, 3408. See also
14. b) P. Brownbridge, T.-H. Chan, Tetrahedron Lett. 1980, 21, 3427.
15. a) C. H. Heathcock, K. T. Hug, L. A. Flippin, Tetrahedron Lett. 1984, 25, 5973
16. b) C. H. Heathcock, S. K. Davidsen, K. T. Hug, L. A. Flippin, J. Org. Chem. 1986, 51, 3027. For the application to monosaccharide synthesis, see
17. c) C. H. Heathcock, S. H. Montgomery, Tetrahedron Lett. 1985, 26, 1001
18. d) S. H. Montgomery, M. C. Pirrung, C. H. Heathcock, Carbohydr. Res. 1990, 202, 13.
19. a) M. T. Reetz, K. Kesseler, A. Jung, Tetrahedron Lett. 1984, 25, 729
20. b) M. T. Reetz, K. Kesseler, A. Jung, Tetrahedron 1984, 40, 4327
21. c) M. T. Reetz, Angew. Chem., Int. Ed. Engl. 1984, 23, 556
22. d) M. T. Reetz, K. Kesseler, J. Org. Chem. 1985, 50, 5434. See also other related studies
23. e) M. T. Reetz, K. Kesseler, S. Schmidtberger, B. Wenderoth, R. Steinbach, Angew. Chem., Int. Ed. Engl. 1983, 22, 989. For a recent review of the chelation-controlled Mukaiyama aldol reaction of chiral α- and β-alkoxy aldehydes, see
24. f) G.-D. Roiban, A. Ilie, M. T. Reetz, Chem. Lett. 2014, 43, DOI: 10.1246/cl.130920.
25. a) C. Gennari, A. Bernardi, G. Poli, C. Scolastico, Tetrahedron Lett. 1985, 26, 2373
26. b) C. Gennari, M. G. Beretta, A. Bernardi, G. Moro, C. Scolastico, R. Todeschini, Tetrahedron 1986, 42, 893
27. c) C. Gennari, P. G. Cozzi, Tetrahedron 1988, 44, 5965
28. d) C. Gennari, in Comprehensive Organic Synthesis (Eds.:, B. M. Trost, I. Fleming,), Pergamon Press, Oxford, 1991, Vol. 2, pp. 629-660. See also other related studies
29. e) C. Gennari, P. G. Cozzi, J. Org. Chem. 1988, 53, 4015
30. f) R. Annunziata, M. Cinquini, F. Cozzi, P. G. Cozzi, E. Consolandi, J. Org. Chem. 1992, 57, 456.
31. a) W. R. Ewing, B. D. Harris, W.-R. Li, M. M. Joullié, Tetrahedron Lett. 1989, 30, 3757
32. b) W.-R. Li, W. R. Ewing, B. D. Harris, M. M. Joullié, J. Am. Chem. Soc. 1990, 112, 7659.
33. C. Mukai, M. Miyakawa, M. Hanaoka, J. Chem. Soc., Perkin Trans. 1 1997, 913.
34. a) M. T. Reetz, S.-H. Kyung, C. Bolm, T. Zierke, Chem. Ind. 1986, 824
35. b) Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008.
36. a) S. Kobayashi, T. Mukaiyama, Chem. Lett. 1989, 18, 297
37. b) S. Kobayashi, H. Uchiro, Y. Fujishita, I. Shiina, T. Mukaiyama, J. Am. Chem. Soc. 1991, 113, 4247.
38. a) T. Mukaiyama, H. Uchiro, S. Kobayashi, Chem. Lett. 1989, 18, 1001
39. b) T. Mukaiyama, H. Uchiro, S. Kobayashi, Chem. Lett. 1989, 18, 1757.
40. a) S. Kobayashi, T. Sano, T. Mukaiyama, Chem. Lett. 1989, 18, 1319
41. b) T. Mukaiyama, S. Kobayashi, T. Sano, Tetrahedron 1990, 46, 4653.
42. S. Kobayashi, Y. Fujishita, T. Mukaiyama, Chem. Lett. 1989, 18, 2069.
43. a) T. Mukaiyama, S. Kobayashi, H. Uchiro, I. Shiina, Chem. Lett. 1990, 19, 129
44. b) S. Kobayashi, A. Ohtsubo, T. Mukaiyama, Chem. Lett. 1991, 20, 831
45. c) T. Mukaiyama, M. Furuya, A. Ohtsubo, S. Kobayashi, Chem. Lett. 1991, 20, 989
46. d) S. Kobayashi, H. Uchiro, I. Shiina, T. Mukaiyama, Tetrahedron 1993, 49, 1761.
47. a) S. Kobayashi, Y. Fujishita, T. Mukaiyama, Chem. Lett. 1990, 19, 1455
48. b) S. Kobayashi, M. Furuya, A. Ohtsubo, T. Mukaiyama, Tetrahedron: Asymmetry 1991, 2, 635.
49. T. Mukaiyama, H. Uchiro, S. Kobayashi, Chem. Lett. 1990, 19, 1147.
50. S. Kobayashi, T. Kawasuji, N. Mori, Chem. Lett. 1994, 23, 217.
51. a) T. Mukaiyama, H. Uchiro, I. Shiina, S. Kobayashi, Chem. Lett. 1990, 19, 1019
52. b) T. Mukaiyama, I. Shiina, H. Uchiro, S. Kobayashi, Bull. Chem. Soc. Jpn. 1994, 67, 1708.
53. T. Mukaiyama, I. Shiina, S. Kobayashi, Chem. Lett. 1991, 20, 1901.
54. S. Kobayashi, M. Horibe, Y. Saito, Tetrahedron 1994, 50, 9629.
55. S. Kobayashi, M. Horibe, J. Am. Chem. Soc. 1994, 116, 9805.
56. S. Kobayashi, M. Horibe, Synlett 1994, 147.
57. S. Kobayashi, I. Shiina, J. Izumi, T. Mukaiyama, Chem. Lett. 1992, 21, 373.
58. T. Mukaiyama, I. Shiina, J. Izumi, S. Kobayashi, Heterocycles 1993, 35, 719.
59. a) S. Kobayashi, T. Kawasuji, Tetrahedron Lett. 1994, 35, 3229
60. b) S. Kobayashi, M. Horibe, I. Hachiya, Tetrahedron Lett. 1995, 36, 3173.
61. S. Kobayashi, T. Hayashi, J. Org. Chem. 1995, 60, 1098.
62. S. Kobayashi, T. Kawasuji, Synlett 1993, 911.
63. S. Kobayashi, M. Horibe, M. Matsumura, Synlett 1995, 675.
64. I. Shiina, R. Ibuka, Tetrahedron Lett. 2001, 42, 6303.
65. I. Shiina, Y. Yamai, T. Shimazaki, J. Org. Chem. 2005, 70, 8103.
66. I. Shiina, T. Iizumi, Y. Yamai, Y. Kawakita, K. Yokoyama, Y. Yamada, Synthesis 2009, 2915.
67. a) S. Kobayashi, M. Horibe, Tetrahedron: Asymmetry 1995, 6, 2565
68. b) S. Kobayashi, M. Horibe, Tetrahedron 1996, 52, 7277
69. c) S. Kobayashi, M. Horibe, Chem. Eur. J. 1997, 3, 1472.
70. S. Kobayashi, M. Horibe, Chem. Lett. 1995, 24, 1029.
71. a) G. J. McGarvey, M. Kimura, T. Oh, J. M. Williams, J. Carbohydr. Chem. 1984, 3, 125
72. b) T. Mukaiyama, K. Suzuki, T. Yamada, F. Tabusa, Tetrahedron 1990, 46, 265.
73. T. Mukaiyama, I. Shiina, S. Kobayashi, Chem. Lett. 1990, 19, 2201.
74. T. Mukaiyama, H. Anan, I. Shiina, S. Kobayashi, Bull. Soc. Chim. Fr. 1993, 130, 388.
75. S. Kobayashi, S. Onozawa, T. Mukaiyama, Chem. Lett. 1992, 21, 2419.
76. I. Shiina, H. Fukui, in Acid Catalysis in Modern Organic Synthesis (Eds.:, H. Yamamoto, K. Ishihara,), Wiley-VCH, Weinheim, 2008, Vol. 1, pp. 517-550.
77. a) Y. Kanda, T. Fukuyama, J. Am. Chem. Soc. 1993, 115, 8451
78. b) T. Fukuyama, Y. Kanda, J. Synth. Org. Chem., Jpn. 1994, 52, 888.
79. J. D. White, J. Derrberg, Chem. Commun. 1997, 1919.
80. a) S. Kobayashi, T. Hayashi, T. Kawasuji, Tetrahedron Lett. 1994, 35, 9573
81. b) S. Kobayashi, T. Furuta, Tetrahedron 1998, 54, 10275.
82. a) S. Kobayashi, T. Hayashi, S. Iwamoto, T. Furuta, M. Matsumura, Synlett 1996, 672
83. b) S. Kobayashi, M. Matsumura, T. Furuta, T. Hayashi, S. Iwamoto, Synlett 1997, 301
84. c) S. Kobayashi, T. Furuta, T. Hayashi, M. Nishijima, K. Hanada, J. Am. Chem. Soc. 1998, 120, 908.
85. T. Wakabayashi, K. Mori, S. Kobayashi, J. Am. Chem. Soc. 2001, 123, 1372.
86. a) S. Kobayashi, M. Ueno, R. Suzuki, H. Ishitani, Tetrahedron Lett. 1999, 40, 2175
87. b) S. Kobayashi, M. Ueno, R. Suzuki, H. Ishitani, H.-S. Kim, Y. Wataya, J. Org. Chem. 1999, 64, 6833.
88. a) I. Shiina, H. Iwadare, H. Sakoh, M. Hasegawa, Y. Tani, T. Mukaiyama, Chem. Lett. 1998, 27, 1
89. b) I. Shiina, K. Saitoh, I. Fréchard-Ortuno, T. Mukaiyama, Chem. Lett. 1998, 27, 3
90. c) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada, K. Saitoh, Chem. Eur. J. 1999, 5, 121.
91. K. Saitoh, I. Shiina, T. Mukaiyama, Chem. Lett. 1998, 27, 679.
92. a) I. Shiina, Y, Fukuda, T. Ishii, H. Fujisawa, T. Mukaiyama, Chem. Lett. 1998, 27, 831
93. b) I. Shiina, H. Fujisawa, T. Ishii, Y. Fukuda, Heterocycles 2000, 52, 1105.
94. I. Shiina, Tetrahedron 2004, 60, 1587.
95. I. Shiina, Y. Kawakita, R. Ibuka, K. Yokoyama, Y. Yamai, Chem. Commun. 2005, 4062.
96. The first total synthesis of buergerinin G was achieved by Lowary et al. using the successful oxygenation of buergerinin F, see:, J.-S. Han, T. L. Lowary, J. Org. Chem. 2003, 68, 4116.
97. a) I. Shiina, H. Oshiumi, M. Hashizume, Y. Yamai, R. Ibuka, Tetrahedron Lett. 2004, 45, 543
98. b) I. Shiina, M. Hashizume, Y. Yamai, H. Oshiumi, T. Shimazaki, Y. Takasuna, R. Ibuka, Chem. Eur. J. 2005, 11, 6601.
99. a) Y. Guindon, Z. Liu, G. Jung, J. Am. Chem. Soc. 1997, 119, 9289
100. b) J.-P. Bouvier, G. Jung, Z. Liu, B. Guérin, Y. Guindon, Org. Lett. 2001, 3, 1391
101. c) Y. Guindon, K. Houde, M. Prévost, B. Cardinal-David, S. R. Landry, B. Daoust, M. Bencheqroun, B. Guérin, J. Am. Chem. Soc. 2001, 123, 8496
102. d) Y. Guindon, M. Prévost, P. Mochirian, N. Guérin, Org. Lett. 2002, 4, 1019
103. e) P. Mochirian, B. Cardinal-David, B. Guérin, M. Prévost, Y. Guindon, Tetrahedron Lett. 2002, 43, 7067.
104. For the ester and lactone synthesis: a), I. Shiina, M. Kubota, H. Oshiumi, M. Hashizume, J. Org. Chem. 2004, 69, 1822
105. b) I. Shiina, H. Fukui, A. Sasaki, Nat. Protoc. 2007, 2, 2312
106. c) I. Shiina, Chem. Rev. 2007, 107, 239
107. d) I. Shiina, T. Katoh, S. Nagai, M. Hashizume, Chem. Rec. 2009, 9, 305
108. e) I. Shiina, Y. Umezaki, N. Kuroda, T. Iizumi, S. Nagai, T. Katoh, J. Org. Chem. 2012, 77, 4885
109. f) I. Shiina, Bull. Chem. Soc. Jpn. 2014. DOI: 10.1246/bcsj.20130216.
110. For the amide and peptide synthesis: a), I. Shiina, Y. Kawakita, Tetrahedron 2004, 60, 4729
111. b) I. Shiina, H. Ushiyama, Y. Yamada, Y. Kawakita, K. Nakata, Chem. Asian J. 2008, 3, 454.
112. H. Uchiro, K. Nagasawa, T. Kotake, D. Hasegawa, A. Tomita, S. Kobayashi, Bioorg. Med. Chem. Lett. 2002, 12, 2821.
113. I. Shiina, Y. Takasuna, R. Suzuki, H. Oshiumi, Y. Komiyama, S. Hitomi, H. Fukui, Org. Lett. 2006, 8, 5279.
114. I. Shiina, H. Fukui, Chem. Commun. 2009, 385.
115. a) H. Fukui, I. Shiina, Org. Lett. 2008, 10, 3153
116. b) H. Fukui, S. Hitomi, R. Suzuki, T. Ikeda, Y. Umezaki, K. Tsuji, I. Shiina, Tetrahedron Lett. 2008, 49, 6514
117. c) H. Fukui, K. Tsuji, Y. Umezaki, I. Shiina, Heterocycles 2009, 79, 403.
118. T. Nagasawa, S. Kuwahara, Org. Lett. 2013, 15, 3002.
119. I. Shiina, Y. Umezaki, Y. Ohashi, Y. Yamazaki, S. Dan, T. Yamori, J. Med. Chem. 2013, 56, 150.