A novel utilization of acylsilanes in organic synthesis

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 68, Issue 6, 2010, Pages 601-613

  Honda, Mitsunori ^a   Segi, Masahito ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

1,2,3 triol; 1,3 diol; Acylsilane; Aldol Tishchenko reaction; Homoallylic rearrangement; Mukaiyama aldol reaction; Nudeophilic addition; Protodesilylation; Silyl group; Stereoselective synthesis

Indexed keywords

ADDITION REACTIONS; CHEMICAL REACTIONS; CONDENSATION REACTIONS; KETONES; STEREOCHEMISTRY;

1,2,3-TRIOL; 1,3-DIOL; ACYLSILANE; ALDOL-TISHCHENKO REACTION; HOMOALLYLIC REARRANGEMENT; MUKAIYAMA ALDOL REACTION; NUDEOPHILIC ADDITION; PROTODESILYLATION; SILYL GROUP; STEREOSELECTIVE SYNTHESIS;

STEREOSELECTIVITY;

EID: 77956162145     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.68.601     Document Type: Article

References (71)

1. M. A. Brook, "Silicon in Organic, Organometallic, and Polymer Chemistry" John Wiley & Sons, New York, 2000.
2. P. C. B. Page, M. J. McKenzie, S. S. Klair, S. Rosenthal, "The Chemistry of Organic Silicon Compounds" eds. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, UK, 1998, Vol. 2, Chap. 27, p 1599;
3. B. F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, A. Ricci, J. Organometal. Chem., 567,181 (1998)
4. A. G. Brook, J. Am. Chem. Soc., 79, 4373 (1957).
5. A. G. Brook, M. A. Quigley, G. J. C. Peddle, N. V. Schwartz, C. M. Warner, J. Am. Chem. Soc., 82, 5102 (1960).
6. P. C. B. Page, S. Rosenthal, Tetrahedron, 46, 2573 (1990).
7. F. Bernardi, L. Lunazzi, A. Ricci, G. Seconi, G. Tonachini, Tetrahedron, 42, 3607 (1986)
8. J. P. Picard, J. M. Aizpurua, A. Elyusufi, P. Kowalski, J. (26 )Organomet. Chem., 391, 13 (1990);
9. J.-B. Verlhac, H. Kwon, M. Pereyre, J. Organomet. Chem., 437, 13 (1992).
10. B. H. Lipshutz, C. Lindsley, R. Susfalk, T. Gross, Tetrahe dron Lett., 35,8999 (1994)
11. T. Nakajima, M. Tanabe, K. Ohno, M. Segi, S. Suga, Chem. Lett., 1986,177
12. H. J. Reich, J. J. Rusek, R. E. Olson, J. Am. Chem. Soc, 101, 2225 (1979)
13. A. Ricci, A. Degl'Innocenti, S. Chimichi, M. Fiorenza, G. Rossini, J. Bestmann, J. Org. Chem., 50, 130 (1985);
14. J. A. Miller, G. Zweifel, J. Am. Chem. Soc, 103, 6217 (1981);
15. P. C. B. Page, S. Rosenthal, R. V. Williams, Tetrahedron Lett., 28,4455 (1987)
16. R. Mahrwald, "Modern Aldol Reactions" ed. by R. Mahrwald, Wiley-VCH, Weinheim, 2004
17. M. Honda, R. Iwamoto, Y. Nogami, M. Segi, Chem. Lett., 34, 466 (2005)
18. I. Kuwajima, K. Matsumoto, S. Sugahara, Chem. Lett., 1980, 525
19. D. Schinzer, Synthesis, 1989,179
20. M. Shibasaki, T. Ohshima, "Asymmetric Synthesis" eds. by M. Christmann, S. BrSse, Wiley-VCH, Weinheim, 2007, p 141;
21. Y. Horiuchi, V. Gnanadesikan, T. Ohshima, H. Masu, K. Katagiri, Y. Sei, K. Yamaguchi, M. Shibasaki, Chem. Eur. J., 11, 5195 (2005);
22. V. Gnanadesikan, Y. Horiuchi, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc, 126, 7782 (2004);
23. M. Stodulski, J. Jazwinski, J. Mlynarski, Eur. J. Org. Chem., 2008, 5553.
24. C. M. Mascarenhas, S. P. Miller, P. S. White, J. P. Morken, Angew. Chem. Int. Ed., 40, 601 (2001)
25. L. Lu, H.-Y. Chang, J.-M. Fang, J. Org. Chem., 64, 843 (1999);
26. D. Enders, S. J. Ince, M. Bonnekessel, J. Runsink, G. Raabe, Synlett, 2002, 962.
27. M. Markert, R. Mahrwald, Synthesis, 2004,1429.
28. T. Mukaiyama, K. Narasaka, K. Banno, Chem. Lett., 1973, 1011.
29. T. Mukaiyama, K. Banno, K. Narasaka, J. Am. Chem. Soc, 96, 7503 (1974).
30. K. Saigo, M. Osaki, T. Mukaiyama, Chem. Lett., 1975, 989
31. T. Sato, M. Arai, I. Kuwajima, J. Am. Chem. Soc, 99, 5827 (1977)
32. M. Honda, W. Oguchi, M. Segi, T. Nakajima, Tetrahedron, 58, 6815 (2002)
33. I. R. Silverman, C. Edington, J. D. Elliott, W. S. Johnson, J. Org. Chem., 52, 180 (1987).
34. M. Kinugasa, T. Harada, K. Fujita, A. Oku, Synlett, 1996,43.
35. H. Heathcock, S. K. Davidsen, K. T. Hug, L. A. Flippin, J. Org. Chem., 51,3027(1986)
36. A. P. Davis, S. J. Plunkett, J. E. Muir, J. Chem. Soc, Chem. Commun., 1998,1797
37. I. Mori, K. Ishihara, L. A. Flippin, K. Nozaki, H. Yamamoto, P. A. Bartlett, H. Heathcock, J. Org. Chem., 55, 6107 (1990)
38. M. Nakada, Y. Urano, S. Kobayashi, M. Ohno, J. Am. Chem. Soc, 110, 4826 (1988 );
39. M. Nakada, Y. Urano, S. Kobayashi, M. Ohno, Tetrahedron Lett., 35, 741 (1994);
40. P. F. Cirillo, S. Panek, J. Org. Chem., 59, 3055 (1994);
41. A. Yanagisawa, S. Habaue, H. Yamamoto, Tetrahedron, 48, 1969 (1992);
42. K. Tanaka, K. Takeda, Tetrahedron Lett., 45, 7859 (2004);
43. M. Sasaki, E. Kawanishi, Y. Nakai, T. Matsumoto, K. Yamaguchi, K. Takeda, J. Org. Chem., 68, 9330 (2003);
44. K. Takeda, K. Yamawaki, N. Hatakeyama, J. Org. Chem., 67, 1786 (2002).
45. M. Shindo, K. Matsumoto, S. Mori, K. Shishido, J. Am. Chem. Soc, 124, 6840 (2002).
46. A. Kamimura, Y. Kaneko, A. Ohta, K. Matsuura, Y. Fujimoto, A. Kakehi, S. Kanemasa, Tetrahedron, 58, 9613 (2002)
47. M. Honda, N. Ohkura, S.-I. Saisyo, M. Segi, T. Nakajima, Tetrahedron, 59,8203 (2003)
48. M, Honda, Y. Mikami, T. Sanjyo, M. Segi, T. Nakajima, Chem. Lett., 34, 1432 (2005).
49. K. Morihata, Y. Horiuchi, M. Taniguchi, K. Oshima, K. Utimoto, Tetrahedron Lett., 36, 5555 (1995);
50. A. G. Brook, N. V. Schwartz, J. Org. Chem., 27, 2311 (1962)
51. P. Huber, S. Bratovanov, S. Bienz, C. Syldatk, M. Pietzsch, Tetrahedron: Asymmetry, 7,69 (1996)
52. E. A. Mash, K. A. Nelson, S. Van Deusen, S. B. Hemperly, Org. Synth. Coll. Vol. VIII, John Wiley and Sons. Inc. New York, 1993, p 155
53. T. Nishizawa, K. Nakae, M. Honda, K.-K. Kunimoto, M. Segi, Tetrahedron Lett., 51,1294 (2010)
54. S. Ono, S. Shuto, A. Matsuda, Tetrahedron Lett., 37, 221 (1996);
55. M. Lautens, P. H. M. Delanghe, J. Org. Chem., 60, 2474 (1995).
56. J. Clayden, D. W. Watson, M. Chambers, Tetrahe. dron, 61, 3195 (2005).
57. K. Nomura, S. Matsubara, Synlett, 9, 1412 (2008).
58. Y. Yamauchi, G. Onodera, K. Sakata, M. Yuki, Y. Miyake, S. Uemura, Y. Nishibayashi, J. Am. Chem. Soc, 129, 5175 (2007);
59. M. Julia, S. Julia, R. Guegan, Bull. Soc. Chim. Fr., 1960, 1072.
60. M. Julia, S. Julia, S.-Y. Tchen, Bull. Soc Chim.Fr, 1961,1849.
61. Y. Maeda, T. Nishimura, S. Uemura, Chem. Lett., 34, 380 (2005)
62. M. Honda, T. Nishizawa, Y. Nishii, S. Fujinami, M. Segi, Tetrahedron, 65, 9403 (2009);
63. M. Honda, T. Nishizawa, Y. Nishii, M. Segi, T. Nakajima, Chem. Lett., 37, 946 (2008);
64. M. Honda, T. Nishizawa, T. Sano, M. Segi, T. Nakajima, Tetra hedron Lett., 47, 5751 (2006);
65. K. Sakaguchi, M. Higashino, Y. Ohfune, Tetrahedron, 59, 6647 (2003);
66. K. Sakaguchi, M. Fujita, Y. Ohfune, Tetrahedron Lett., 39,4313 (1998)
67. M. Honda, Y. Yamamoto, H, Tsuchida, M. Segi, T. Nakajima, Tetrahedron Lett., 46, 6465 (2005)
68. J. Haywood-Farmer, Chem. Rev., 74, 315 (1974);
69. C. F. Wilcox, L. M. Loew, R. Hoffmann, J. Am. Chem. Soc, 95, 8192 (1973)
70. R. J.-R. Hwu, S.-C. Tsay, B.-L. Cheng, "The Chemistry of Organic Silicon Compounds" eds. by Z. Rappoport, Y. Apeloig, Wiley, Chichester, UK, 1998, Vol. 2, Chap. 8, p 431.
71. H. Oda, M. Sato, Y. Morisawa, K. Oshima, H. Nozaki, Tetra hedron Lett., 24, 2877 (1983)