Enantioselective michael addition of β-keto esters to methyl vinyl ketone employing a chiral N, N’-dioxide-scandium trifluoromethanesulfonate complex as a catalyst

Chemical Communications

Volumn 1, Issue 17, 2001, Pages 1596-1597

  Nakajima, Makoto ^a   Yamaguchi, Yukiko ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; KETONE DERIVATIVE; OXIDE; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CATALYST; CHEMICAL REACTION; CHIRALITY; REACTION ANALYSIS; TECHNIQUE;

EID: 0035823304     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/b104876g     Document Type: Article

References (28)

1. B. E. Rossiter and N. M. Swingle, Chem. Rev, 1992, 92, 771.
2. M. Shibasaki, H. Sasai and T. Arai, Angew. Chem., Int. Ed. Engl., 1997, 36, 1236.
3. J. Christoffers, Eur. J. Org. Chem., 1998, 1259.
4. J. Leonard, E. Diez-Barra and S. Merino, Eur. J. Org. Chem, 1998, 2051.
5. H. Wynberg and R. Helder, Tetrahedron Lett, 1975, 4057.
6. K. Hermann and H. Wynberg, J. Org. Chem., 1979, 44, 2238.
7. N. Kobayashi and K. Iwai, J. Am. Chem. Soc, 1978, 100, 7071.
8. D. J. Cram and G. D. J. Sogah, J. Chem. Soc., Chem. Commun., 1981, 625.
9. H. Brunner and H. Benedikt, Angew. Chem., Int. Ed. Engl, 1984, 23, 312.
10. G. Desimoni, P. Quadrelli and P. P. Righetti, Tetrahedron, 1990, 46, 2927.
11. C. Botteghi, S. Paganelli, A. Schionato, C. Boga and A. Fava, J. Mol. Catal., 1991, 66, 7.
12. Y. Tamai, A. Kamifuku, E. Koshiishi and S. Miyano, Chem. Lett, 1995, 957.
13. N. M. Karayannis, L. L. Pytlewski and C. M. Mikulski, Coord. Chem. Rev., 1973, 11, 93.
14. M. B. Diana, M. Marchetti and G. Melloni, Tetrahedron: Asymmetry, 1995, 6, 117.
15. I. A. O'Neil, C. D. Turner and S. B. Kalindjian, Synlett, 1997, 777.
16. G. Dyker, B. Hölzer and G. Henkel, Tetrahedron: Asymmetry, 1999, 10, 3297.
17. V. Derdau, S. Laschat, E. Hupe, W. A. König, I. Dix and P. G. Jones, Eur. J. Inorg. Chem, 1999, 1001.
18. K. Miura and T. Katsuki, Synlett, 1999, 783.
19. M. Nakajima, Y. Sasaki, M. Shiro and S. Hashimoto, Tetrahedron: Asymmetry, 1997, 8, 341.
20. M. Nakajima, Y. Sasaki, H. Iwamoto and S. Hashimoto, Tetrahedron Lett, 1998, 39, 87.
21. M. Nakajima, M. Saito, M. Shiro and S. Hashimoto, J. Am. Chem. Soc, 1998, 120, 6419.
22. M. Nakajima, M. Saito and S. Hashimoto, Chem. Pharm. Bull., 2000, 48, 306.
23. M. Saito, M. Nakajima and S. Hashimoto, Chem. Commun, 2000, 1851.
24. M. Saito, M. Nakajima and S. Hashimoto, Tetrahedron, 2000, 56, 9589.
25. S. Kobayashi, Eur. J. Org. Chem, 1999, 15.
26. S. Kobayashi, M. Araki and I. Hachiya, J. Org. Chem, 1994, 59, 3758.
27. S. Kobayashi, H. Ishitani, M. Araki and I. Hachiya, Tetrahedron Lett, 1994, 35, 6325.
28. H. Kodama, J. Ito, K. Hori, T. Ohta and I. Furusawa, J. Organomet. Chem., 2000, 603, 6.