Trends in asymmetric Michael reactions catalysed by tripeptides in combination with an achiral additive in different solvents

European Journal of Organic Chemistry

Volumn , Issue 19, 2004, Pages 4014-4019

  Tsogoeva, Svetlana B ^a   Jagtap, Sunil B ^a   Ardemasova, Zoya A ^b   Kalikhevich, Victor N ^b  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

Asymmetric catalysis; Michael addition; Organocatalyst; Peptides

Indexed keywords

ACETONE; DIMETHYL SULFOXIDE; SOLVENT; TRIPEPTIDE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; MICHAEL ADDITION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 5444250671     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400243     Document Type: Article

References (23)

1. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726-2042; Angew. Chem. 2001, 113, 3840-3864.
2. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2001, 40, 3726-2042; Angew. Chem. 2001, 113, 3840-3864.
3. T. Sugimoto, Y. Matsumura, S. Tanimoto, M. Okano, J. Chem. Soc., Chem. Commun. 1978, 926-927.
4. E. R. Jarvo, S. J. Miller, Tetrahedron 2002, 58, 2481-2495.
5. B. List, R. A. Lerner, C. F. Barbas III, J. Am. Chem. Soc. 2000, 122, 2395-2396.
6. Z. G. Hajos, D. R. Parrish, J. Org. Chem. 1974, 39, 1615-1621.
7. K. A. Ahrendt, Ch. J. Borths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.
8. S. Hanessian, V. Pham, Org. Lett. 2000, 2, 2975-2978.
9. [8a] M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902.
10. [8b] M. S. Iyer, K. M. Gigstad, N. D. Namdev, M. Lipton, J. Am. Chem. Soc. 1996, 118, 4910-4911.
11. [9a] H. J. Martin, B. List, Synlett 2003, 1901-1902.
12. [9b] B. List, P. Pojarliev, H. J. Martin, Org. Lett. 2001, 3, 2423-2425.
13. M. Yoshikawa, Antiamnesic and anticholesteremic peptides, JP 2002080393, 2002, 7 pp.
14. J. C. Tolle, W. Z. Gifford, K. W. Funk, Antiallergic pentapeptide synthesis, US 5212287, 1993, 9 pp.
15. C. R. Woods, N. Faucher, B. Eschgfaller, K. W. Bair, D. L. Boger, Bioorg. Med. Chem. Lett. 2002, 12, 2647-2650.
16. [13a] See Exp. Sect. for details.
17. [13b] M. V. Ovchinnikov, Z. D. Bespalova, A. S. Molokoedov, I. V. Revenko, N. F. Sepetov, O. L. Isakova, M. I. Titov, Collect. Czech. Chem. Commun. 1989, 54, 772-783.
18. [13c] V. I. Unkovskii, G. A. Vasil'eva, R. P. Evstigneeva, J. Gen. Chem. USSR 1986, 56, 1455-1460.
19. M. Tamaki, G. Han, V. J. Hruby, J. Org. Chem. 2001, 66, 1038-1042.
20. See Exp. Sect. for details.
21. A. Berthod, S. Carda-Broch, The Annals of the Marie Curie Fellowships, vol. 3, http://www.mariecurie.org/annals/volume3/berthod.pdf
22. [17a] J. F. Coetzee, G. R. Padmanabhan, J. Am. Chem. Soc. 1965, 87, 5005-5010.
23. [17b] B. W. Clare, D. Cook, E. C. F. Ko, Y. C. Mac, A. J. Parker, J. Am. Chem. Soc. 1966, 88, 1911-1916.