Functionalized 2-chlorocyclopropanecarboxylates through the MIRC reaction

Synlett

Volumn , Issue 6, 2005, Pages 976-980

  Giubellina, Nicola ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

amino acid; 3,3 dihalo 1 azaallylic anion; Activated olefin; Halogenated cyclopropane; MIRC reaction

Indexed keywords

2 (AMINOMETHYL) 2 CHLOROCYCLOPROPANECARBOXYLATE; 2 ACYL 2 CHLOROCYCLOPROPYLCARBOXYLATE; 2 CHLORO 2 IMIDOYLCYCLOPROPANECARBOXYLATE; 2 CHLOROCYCLOPROPANECARBOXYLATE DERIVATIVE; 3,3 DICHLORO 1 AZAALLYLIC ANION; ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; ANION; CYCLOPROPANE; CYCLOPROPANECARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; HALOGENATION; MICHAEL INDUCED RING CLOSURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 17144395511     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864800     Document Type: Article

References (28)

1. Zwanenburg, B.; De Kimpe, N. In Houben-Weyl, 4th ed., Vol. E17a; de Meijere, A., Ed.; Thieme: Stuttgart, 1997, 69.
2. (a) Chanjuan Xi, C. C.; Jiang, Y.; Hong, X. Tetrahedron Lett. 2004, 45, 6067.
3. (b) Fouchet, B.; Joucla, M.; Messager, J. C.; Toupet, L. J. Chem. Soc., Chem. Commun. 1982, 859.
4. (c) Joucla, M.; Fouchet, B.; Le Brun, J.; Hamelin, J. Tetrahedron Lett. 1985, 26, 1221.
5. (a) Joucla, M.; El Goumzili, M.; Fouchet, B. Tetrahedron Lett. 1986, 27, 1677.
6. (b) Chavan, S. P.; Venkatraman, M. S.; Sharma, A. K.; Chittiboyina, A. G. Tetrahedron Lett. 1996, 37, 2857.
7. (c) Zindel, J.; de Mejiere, A. Synthesis 1994, 190.
8. (a) Enders, D.; Scherer, H. J.; Raabe, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1664.
9. (b) Enders, D.; Scherer, H. J.; Runsink, J. Chem. Ber. 1993, 126, 1929.
10. (c) Pohlman, M.; Kazmaier, U. Org. Lett. 2003, 5, 2631.
11. Oudeyer, S.; Aaziz, A.; Léonel, E.; Paugam, J. P.; Nédélec, J.-Y. Synlett 2003, 485.
12. Sengmany, S.; Léonel, E.; Paugman, J. P.; Nédélec, J.-Y. Synlett 2002, 533.
13. Nakano, Y.; Hamaguchi, M.; Nagai, T. J. Org. Chem. 1989, 54, 1135.
14. For a recent review on natural products containing cyclopropyl groups see: Donaldson, W. A. Tetrahedron 2001, 57, 8589.
15. (a) Briley, M. Drug Future 1986, 11, 21.
16. (b) Bonnaud, B.; Cousse, H.; Mouzin, G.; Briley, M.; Stenger, A.; Fauran, F.; Couzinier, J.-P. J. Med. Chem. 1987, 30, 318.
17. (c) Kazuta, Y.; Tsujita, R.; Ogawa, K.; Hokonohara, T.; Yamashita, K.; Morino, K.; Matsuda, A.; Shuto, S. Bioorg. Med. Chem. 2002, 10, 1777.
18. For reviews on α-halogenated imines see: (a) De Kimpe, N.; Schamp, N. Org. Prep. Proced. Int. 1979, 11, 115.
19. (b) De Kimpe, N.; Verhé, R.; De Buyck, L.; Schamp, N. Org. Prep. Proced. Int. 1980, 12, 49.
20. (c) Giubellina, N.; Aelterman, W.; De Kimpe, N. Pure Appl. Chem. 2003, 75, 1433.
21. (d) Mangelinckx, S.; Giubellina, N.; De Kimpe, N. Chem. Rev. 2004, 104, 2353.
22. (a) De Kimpe, N.; Coppens, W.; Welch, J.; De Corte, B. Synthesis 1990, 675.
23. (b) Aelterman, W.; De Kimpe, N.; Declercq, J.-P. J. Org. Chem. 1998, 63, 6.
24. Akabori, S.; Yoshii, T. Tetrahedron Lett. 1978, 19, 4523.
25. 3 after 45 h at r.t. to a mixture of E/Z = 66:34.
26. Kamitani, A.; Chatani, N.; Morimoto, T.; Murai, S. J. Org. Chem. 2000, 65, 9230.
27. f = 0.47).
28. f = 0.35).