Dimethylsilyl ketene acetal as a nucleophile in asymmetric Michael reaction: Enhanced enantioselectivity in oxazaborolidinone-catalyzed reaction

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4877-4879

  Harada, Toshiro ^a   Adachi, Shinya ^a   Wang, Xiaowei ^a  

^a KYOTO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; KETENE DERIVATIVE; PROPOFOL; SILICON;

ANALYTIC METHOD; ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION ANALYSIS;

EID: 12344335546     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048071g     Document Type: Article

References (36)

1. Review: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1. (b) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (d) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
2. Review: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1. (b) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (d) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
3. Review: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1. (b) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (d) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
4. Review: (a) Tomioka, K.; Nagaoka, Y. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, Chapter 31.1. (b) Kanai, M.; Shibasaki, M. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley: New York, 2000; p 569. (c) Sibi, M.; Manyem, S. Tetrahedron 2000, 56, 8033. (d) Krause, N.; Hoffmann-Röder, A. Synthesis 2001, 171.
5. For leading references, see: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2582. (c) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
6. For leading references, see: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2582. (c) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
7. For leading references, see: (a) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520. (b) Harada, S.; Kumagai, N.; Kinoshita, T.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 2582. (c) Itoh, K.; Kanemasa, S. J. Am. Chem. Soc. 2002, 124, 13394.
8. (a) Sawamura, H.; Hamashima, H.; Ito, Y. J. Am. Chem. Soc. 1992, 114, 8295.
9. (b) Yamaguchi, M.; Shiraishi, T.; Hirama, M. Angew. Chem., Int. Ed. Engl. 1993, 32, 1176.
10. (c) Sasai, H.; Arai, T.; Shibasaki, M. J. Am. Chem. Soc. 1994, 116, 1571.
11. (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97.
12. (b) Bernardi, A.; Colombo, G.; Scolastico, C. Tetrahedron Lett. 1996, 37, 8921.
13. (c) Bernardi, A.; Karamfilova, K.; Sanguinetti, S.; Scolastico, C. Tetrahedron 1997, 53, 13009.
14. (d) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015.
15. (e) Kitajima, H.; Katsuki, T. Synlett 1997, 568.
16. (f) Nishikori, H.; Ito, K.; Katsuki, T. Tetrahedron: Asymmetry 1998, 9, 1165.
17. (g) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Tedrow, J. S. J. Am. Chem. Soc. 1999, 121, 1994.
18. (h) Evans, D. A.; Willis, M. C.; Johnston, J. N. Org. Lett. 1999, 1, 865.
19. (i) Evans, D. A.; Johnston, J. S.; Olhava, E. J. J. Am. Chem. Soc. 2000, 122, 1635.
20. (j) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, C. W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134.
21. (k) Evans, D. A.; Scheidt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480.
22. (l) Zhang, F.-Y.; Corey, E. J. Org. Lett. 2001, 3, 639.
23. (m) Desimoni, G.; Faita, G.; Filippone, S.; Mella, M.; Zampori, M. G.; Zema, M. Tetrahedron 2001, 57, 10203.
24. (a) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2001, 124, 4370.
25. (b) Austin, J. F.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 1172.
26. (c) Paras, N. A.; MacMillan, D. W. C. J. Am. Chem. Soc. 2002, 124, 7894.
27. (d) Brown, S. P.; Goodwin, N. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 1192.
28. (a) Harada, T.; Iwai, H.; Takatsuki, H.; Fujita, K.; Kubo, M.; Oku, A. Org. Lett. 2001, 3, 2101.
29. (b) Wang, X.; Harada, T.; Iwai, H.; Oku, A. Chirality 2003, 15, 28.
30. (c) Wang, X.; Adachi, S.; Iwai, H.; Takatsuki, K.; Fujita, M.; Kubo, M.; Oku, A.; Harada, T. J. Org. Chem. 2003, 68, 10046.
31. Most recently, Hosomi et al. have reported chloride ion promoted aldol and Michael reactions of DMS enolates. (a) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585. (b) Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. (c) Miura, K.; Nakagawa, T.; Hosomi, A. Synlett 2003, 2068.
32. Most recently, Hosomi et al. have reported chloride ion promoted aldol and Michael reactions of DMS enolates. (a) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585. (b) Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. (c) Miura, K.; Nakagawa, T.; Hosomi, A. Synlett 2003, 2068.
33. Most recently, Hosomi et al. have reported chloride ion promoted aldol and Michael reactions of DMS enolates. (a) Miura, K.; Sato, H.; Tamaki, K.; Ito, H.; Hosomi, A. Tetrahedron Lett. 1998, 39, 2585. (b) Miura, K.; Tamaki, K.; Nakagawa, T.; Hosomi, A. Angew. Chem., Int. Ed. 2000, 39, 1958. (c) Miura, K.; Nakagawa, T.; Hosomi, A. Synlett 2003, 2068.
34. (a) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
35. (b) Carreira, E. M.; Singer, R. A.; Lee, W. J. Am. Chem. Soc. 1994, 116, 8837.
36. (c) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.