A new synthesis of cyanocyclopropanes by the intramolecular alkylation of magnesium carbenoids as the key reaction

Tetrahedron Letters

Volumn 51, Issue 26, 2010, Pages 3380-3384

  Saitoh, Hideki ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Cyanocyclopropane; Cyclopropane; Intramolecular alkylation; Magnesium carbenoid; Multi substituted cyclopropane

Indexed keywords

CARBENOID; CYANIDE; CYCLOPROPANE DERIVATIVE; KETONE DERIVATIVE; MAGNESIUM DERIVATIVE; SULFOXIDE;

ADDITION REACTION; ALKYLATION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION;

EID: 77953121657     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.04.090     Document Type: Article

References (40)

1. Some recent reviews concerning chemistry, synthesis, and synthetic uses of cyclopropanes:. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., and Hudlick T. Chem. Rev. 89 (1989) 165
2. Salaun J. Chem. Rev. 89 (1989) 1247
3. Sonawane H.R., Bellur N.S., Kulkarni D., and Ahuja J.R. Synlett (1993) 875
4. Doyle M.P., and Protopopova M.N. Tetrahedron 54 (1998) 7919
5. Donaldson W.A. Tetrahedron 57 (2001) 8589
6. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977
7. Pietruszka J. Chem. Rev. 103 (2003) 1051
8. Reissig H.-U., and Zimmer R. Chem. Rev. 103 (2003) 1151
9. Kulinkovich O.G. Chem. Rev. 103 (2003) 2597
10. Halton B., and Harvey J. Synlett (2006) 1975
11. Pellissier H. Tetrahedron 64 (2008) 7041
12. Some recent papers concerning synthesis of cyclopropanes by our original methods:. Satoh T., Musashi J., and Kondo A. Tetrahedron Lett. 46 (2005) 599
13. Satoh T., Miura M., Sakai K., and Yokoyama Y. Tetrahedron 62 (2006) 4253
14. Fukushima I., Gouda Y., and Satoh T. Tetrahedron Lett. 48 (2007) 1855
15. Ogata S., Masaoka S., Sakai K., and Satoh T. Tetrahedron Lett. 48 (2007) 5017
16. Yamada Y., Miura M., and Satoh T. Tetrahedron Lett. 49 (2008) 169
17. Miyagawa T., Tatenuma T., Tadokoro M., and Satoh T. Tetrahedron 64 (2008) 5279
18. Satoh T., Nagamoto S., Yajima M., Yamada Y., Ohata Y., and Tadokoro M. Tetrahedron Lett. 49 (2008) 5431
19. Yajima M., Nonaka R., Yamashita H., and Satoh T. Tetrahedron Lett. 50 (2009) 4754
20. Yamada Y., Mizuno M., Nagamoto S., and Satoh T. Tetrahedron 65 (2009) 10025
21. Some recent papers for the synthesis of cyanocyclopropanes:. D'hooghe M., Mangelinckx S., Persyn E., Van Brabandt W., and De Kimpe N. J. Org. Chem. 71 (2006) 4232
22. Barbasiewicz M., Marciniak K., and Fedorynski M. Tetrahedron Lett. 47 (2006) 3871
23. Elinson M.N., Feducovich S.K., Vereshchagin A.N., Gorbunov S.V., Belyakov P.A., and Nikishin G.I. Tetrahedron Lett. 47 (2006) 9129
24. D'hooghe M., Vervisch K., and De Kimpe N. J. Org. Chem. 72 (2007) 7329
25. Liu X.-H., Chen P.-Q., Wang B.-L., Li Y.-H., Wang S.-H., and Li Z.-M. Bioorg. Med. Chem. Lett. 17 (2007) 3784
26. Cao W., Zhang H., Chen J., Deng H., Shao M., Lei L., Qian J., and Zhu Y. Tetrahedron 64 (2008) 6670
27. Chen S., Ma J., and Wang J. Tetrahedron Lett. 49 (2008) 6781
28. Denton J.R., Cheng K., and Davies H.M.L. Chem. Commun. (2008) 1238
29. Mangelinckx S., D'hooghe M., Peeters S., and De Kimpe N. Synthesis (2009) 1105
30. Satoh T., Takano K., Ota H., Someya H., Matsuda K., and Koyama M. Tetrahedron 54 (1998) 5557
31. Satoh T., Kawashima T., Takahashi S., and Sakai K. Tetrahedron 59 (2003) 9599
32. Satoh T., and Ota H. Tetrahedron Lett. 40 (1999) 2977
33. Satoh T., and Ota H. Tetrahedron 56 (2000) 5113
34. Satoh T., and Wakasugi D. Tetrahedron Lett. 44 (2003) 7517
35. Wakasugi D., and Satoh T. Tetrahedron 61 (2005) 1245
36. Satoh T., Ogata S., and Wakasugi D. Tetrahedron Lett. 47 (2006) 7249
37. Ogata S., Saitoh H., Wakasugi D., and Satoh T. Tetrahedron 64 (2008) 5711
38. Doyle M.P., Duffy R., Ratnikov M., and Zhou L. Chem. Rev. 110 (2010) 704
39. Zhang Y., and Doyle M.P. ARKIVOC (2010) 10
40. 3: M, 297.1365. Found: m/z 297.1366.