Michael addition reactions of Grignard reagents to 2-halogenoacrylates: A convenient method for the synthesis of polysubstituted cyclopropane compounds

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 6067-6069

  Chen, Chao ^a   Xi, Chanjuan ^a   Jiang, Yanfeng ^a   Hong, Xiaoyin ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; CYCLOPROPANE DERIVATIVE; HALIDE;

ARTICLE; DRUG SYNTHESIS; GRIGNARD REACTION; MICHAEL ADDITION; QUANTUM YIELD; SUBSTITUTION REACTION;

EID: 3142666937     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.158     Document Type: Article

References (45)

1. De Meijere A. Houblen-Weyl Methods of Organic Chemistry. 4th ed.; Vol. E 17c:1997;Georg Thieme, Stuttgart
2. Burritt A., Coron J.M., Steel P.J. Trends Org. Chem. 4:1993;517-534
3. Davies H.M.L. Tetrahedron. 49:1993;5203-5223
4. Nonhebel D.C. Chem. Soc. Rev. 1993;347-359
5. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Takano J., Hudlicky T. Chem. Rev. 89:1989;165-198
6. Reissig H.-U. Top. Curr. Chem. 144:1988;73-135
7. Paquette L.A. Chem. Rev. 86:1986;733-750
8. Lebel H., Marcoux J.-F., Molinaro C., Charette A.B. Chem. Rev. 103:2003;977-1050
9. Dai L.-X., Hou X.-L., Zhou Y.-G. Pure Appl. Chem. 71:1999;369-376
10. Reissig H.-U. Angew. Chem., Int. Ed. 35:1996;971-973
11. Ohkita M., Nishida S., Tsuji T. Rappoport Z. The Chemistry of the Cyclopropyl Group: Recent Advances in the Synthesis of Cyclopropanes. 1995;261 Wiley, Chichester, UK
12. Brookhart M., Studabaker W.B. Chem. Rev. 87:1987;411-432
13. Little R.D., Dawson J.R. Tetrahedron Lett. 21:1980;2609-2612
14. For selected examples, see: Escribano A., Pedregal C., Gonazález R., Fernández A., Burton K., Stephenson G.A. Tetrahedron. 57:2001;9423-9427
15. Arai S., Nakayama K., Ishida T., Shioiri T. Tetrahedron Lett. 40:1999;4215-4218
16. Shibata I., Mori Y., Yamasaki H., Baba A., Matsuda H. Tetrahedron Lett. 34:1993;6567-6570
17. Hudlicky T., Radesca L., Luna H., Anderson F.E. J. Org. Chem. 51:1986;4746-4748
18. Artaud I., Seyden-Penne J., Viout P. Synthesis. 1980;34-36
19. For other leaving groups, see: Ono N., Yanai T., Hamamoto I., Kamimura A., Kaji A. J. Org. Chem. 50:1985;2807-2809
20. Krief A., De Vos M.I., Sevrin M. Tetrahedron Lett. 27:1986;2283-2287
21. Bhattacharjec S.S., Ila H., Junjappa H. Synthesis. 1982;301-303
22. For sulfur ylides, see: Trost B.M., Melvin L.S. Jr. In Sulfur, Ylides, Emerging Synthetic Intermediates. 1975;Academic Press, New York
23. Li A.-H., Dai L.-X., Aggarwal V.K. Chem. Rev. 97:1997;2341-2372
24. La Porta E., Piarulli U., Cardullo F., Paio A., Provera S., Seneci P., Gennari C. Tetrahedron Lett. 43:2002;761-766
25. For phosphorus ylides, see: Bestmann H.J., Seng F. Angew. Chem. 74:1962;154-157
26. Grieco P.A., Finkelhor R.S. Tetrahedron Lett. 13:1972;3781-3783
27. Lee P.H., Kim J.S., Kim Y.C., Kim S. Tetrahedron Lett. 34:1993;7583-7586
28. Avery T.D., Haselgrove T.D., Rathbone T.J., Taylor D.K., Tiekink E.R.T. Chem. Commun. 1998;333-334
29. Avery T.D., Taylor D.K., Tiekink E.R.T. J. Org. Chem. 65:2000;5531-5546
30. For arsenium ylides, see: Shen Y., Liao Q. Synthesis. 1988;321-323
31. Shen Y., Liao Q. J. Organomet. Chem. 371:1989;31-34
32. Shen Y., Xiang Y. J. Chem. Res. (S). 1994;198-199
33. For telluronium ylides, selected examples see: Tang Y., Huang Y.-Z., Dai L.-X., Sun J., Xia W. J. Org. Chem. 62:1997;954-959
34. Huang Y.-Z., Tang Y., Zhou Z.-L. Tetrahedron. 54:1998;1667-1690
35. Hoppe H.A., Lloyd-Jones G.C., Murray M., Peakman T.M., Walsh K.E. Angew. Chem., Int. Ed. 37:1998;1545-1547
36. Ye S., Yuan L., Hung Z.-Z., Tang Y., Dai L.-X. J. Org. Chem. 65:2000;6257-6260
37. Capps S.M., Clarke T.P., Charmant J.P.H., Hoppe H.A.F., Lloyd-Jones G.C., Murray M., Peakman T.M., Stentiford R.A., Walsh K.E., Worthington P.A. Eur. J. Org. Chem. 2000;963-974
38. Joucal M., Fouchet B., Brun L.E.J., Hamelin J. Tetrahedron Lett. 25:1985;1221-1224
39. Fouchet B., Joucla M., Messager J.C., Toupet L. J. Chem. Soc., Chem. Commun. 1982;858-859
40. Kawakami Y., Tsuruta T. Tetrahedron Lett. 12:1971;1173-1176
41. Tsuruta T., Kawakawi Y. Tetrahedron. 29:1973;1173-1178
42. 2O, see Ref. [13a]
43. Dachon J., Goedken V., Walborsky H.M. J. Org. Chem. 54:1989;1006-1012
44. 4, 306.0467 (100.0%), 308.0446 (97.3%), found 306.0454, 308.0404
45. Marino J.P., Linderman R.J. J. Org. Chem. 46:1981;3696-3702