Chiral scandium catalysts for enantioselective Michael reactions of β-ketoesters

Chemistry - An Asian Journal

Volumn 1, Issue 1-2, 2006, Pages 121-124

  Ogawa, Chikako ^a   Kizu, Keiko ^a   Shimizu, Haruka ^a   Takeuchi, Masahiko ^a   Kobayashi, Shu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Addition reactions; Asymmetric catalysis; Homogeneous catalysis; Lewis acids; Scandium

Indexed keywords

ESTER; SCANDIUM;

ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; ESTERS; SCANDIUM; STEREOISOMERISM;

EID: 33748668448     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200600093     Document Type: Article

References (38)

1. a) M. E. Jung in: Comprehensive Organic Synthesis, Vol. 4 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, New York, 1991, pp. 1-67.
2. b) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, Pergamon, Oxford, 1992.
3. a) M. Kanai, M. Shibasaki in: Catalytic Asymmetric Synthesis, 2nd ed. (Ed.: I. Ojima), Wiley, New York, 2000, pp. 569-592;
4. b) M. Yamaguchi in Comprehensive Asymmetric Catalysis, Vol. 3, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, pp. 1121-1139;
5. c) M. Yamaguchi in Comprehensive Asymmetric Catalysis, Supplement 1, (Eds.: E. N. Jacobsen, A. Pfaltz, and H. Yamamoto), Springer, Berlin, 2004, pp. 151-159;
6. d) J. Christoffers, A. Baro, Angew. Chem. Int. Ed. 2003, 42, 1688;
7. Angew. Chem. 2003, 775, 1726.
8. For example, a) H. Wynberg, R. Helder, Tetrahedron Lett. 1975, 16, 4057;
9. b) N. Kobayashi, K. Iwai, J. Am. Chem. Soc. 1978, 100, 7071;
10. c) Y. Tamai, A. Kamifuku, E. Koshiishi, S. Miyano, Chem. Lett. 1995, 957.
11. D. J. Cram, G. D. Y. Sogah, J. Chem. Soc. Chem. Commun. 1981, 625.
12. Reviews: a) J. Christoffers, Eur. J. Org. Chem. 1998, 1259;
13. b) J. Comelles, M. Moreno-Manas, A. Vallribera, ARKIVOC 2005, 207
14. See also, c) Y. Hamashima, D. Hotta, M. Sodeoka, J. Am. Chem. Soc. 2002, 124, 11240;
15. d) Y. Hamashima, D. Hotta, N. Umebayashi, Y. Tsuchiya, T. Suzuki, M. Sodeoka, Adv. Synth. Catal. 2005, 347, 1576 and references cited therein.
16. Recently, we have developed silver-catalyzed asymmetric Michael reactions in water: a) S. Kobayashi, K. Kakumoto, Y. Mori, K. Manabe, Isr. J. Chem. 2001, 41, 247;
17. b) S. Shirakawa, S. Kobayashi, Synlett in press.
18. Reviews: a) M. Shibasaki, N. Yoshikawa, Chem. Rev. 2002, 102, 2187;
19. b) S. Matsunaga, T. Ohshima, M. Shibasaki, Adv. Synth. Catal. 2002, 344, 3;
20. c) V. Annamalai, E. F. DiMauro, P. J. Carroll, M. C. Kozlowski, J. Org. Chem. 2003, 68, 1973;
21. see also: d) H. Sasai, E. Emori, T. Arai, M. Shibasaki, Tetrahedron Lett. 1996, 37, 5561.
22. a) Lanthanide Triflate-Catalyzed Carbon-Carbon Bond-Forming Reactions in Organic Synthesis: S. Kobayashi in Lanthanides: Chemistry and Use in Organic Synthesis (Ed. : S. Kobayashi), Springer, Heidelberg, 1999, p. 63;
23. b) S. Kobayashi, Eur. J. Org. Chem. 1999, 15;
24. c) S. Kobayashi, Synlett 1994, 689;
25. d) S. Kobayashi, M. Sugiura, H. Kitagawa, W. W.-L. Lam, Chem. Rev. 2002, 102, 2227;
26. e) S. Kobayashi, Chem. Lett. 1991, 2187;
27. f) S. Kobayashi, I. Hachiya, J. Org. Chem. 1994, 59, 3590.
28. S. Kobayashi, M. Araki, I. Hachiya, J. Org. Chem. 1994, 59, 3758.
29. For examples, see: a) D. A. Evans, K. A. Scheldt, K. R. Fandrick, H. W. Lam, J. Wu, J. Am. Chem. Soc. 2003, 125, 10780;
30. b) C. Schneider, A. R. Sreekanth, E. Mai, Angew. Chem. Int. Ed. 2004, 43, 5691;
31. Angew. Chem. 2004, 116, 5809;
32. c) S. Azoulay, K. Manabe, S. Kobayashi, Org. Lett. 2005, 7, 4593.
33. a) M. Nakajima, Y. Yamaguchi, S. Hashimoto, Chem. Commun. 2001, 1596;
34. b) M. Nakajima, S. Yamamoto, Y. Yamaguchi, S. Nakamura, S. Hashimoto, Tetrahedron 2003, 59, 7307.
35. S. Ishikawa, T. Hamada, K. Manabe, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 12236.
36. a) A. Martínez, M. Fernández, J. C. Estévez, R. J. Estévez, L. Castedo, Tetrahedron 2005, 61, 1353;
37. b) I. Sircar, B. L. Duell, M. H. Cain, S. E. Burke, J. A. Bristol, J. Med. Chem. 1986, 29, 2142;
38. c) D. S. Brown, B. A. Marples, P. Smith, L. Walton, Tetrahedron 1995, 51, 3587.