Cyclopropylation of arylamines at the 2-position with cyclopropylmagnesium carbenoids

Tetrahedron

Volumn 65, Issue 48, 2009, Pages 10025-10035

  Yamada, Yukie ^a   Mizuno, Mirai ^a   Nagamoto, Shinobu ^a   Satoh, Tsuyoshi ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

2 Cyclopropylated arylamine; Cyclopropylation; Cyclopropylation of arylamine; Cyclopropylmagnesium carbenoid; Magnesium carbenoid

Indexed keywords

AROMATIC AMINE; CARBENOID; CYCLOPROPANE DERIVATIVE; MAGNESIUM; PHENYL GROUP; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 70350448212     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.096     Document Type: Article

References (31)

1. Barton D.H.R., and Ollis W.D. In: Sutherland I.O. (Ed). Comprehensive Organic Chemistry Vol. 2 (1979), Pergamon, Oxford 131-184
2. Olah G.A., Krishnamurti R., and Surya Prakash G.K. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Chemistry Vol. 3 (1991), Pergamon, Oxford 283-339
3. Li J.J. Name Reactions (2002), Springer, Berlin
4. Mundy B.P., Ellerd M.G., and Favaloro Jr. F.G. Name Reactions and Reagents in Organic Synthesis. 2nd ed. (2005), John Wiley and Sons, Hoboken, New Jersey
5. DePuy C.H. Acc. Chem. Res. 1 (1968) 33
6. Murakami M., and Nishida S. J. Syn. Org. Chem. Jpn. 41 (1983) 22
7. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., and Hudlick T. Chem. Rev. 89 (1989) 165
8. Loeppky R.N., and Elomari S. J. Org. Chem. 65 (2000) 96
9. Yoshida Y., Umezu K., Hamada Y., Atsumi N., and Tabuchi F. Synlett (2003) 2139
10. Gagnon A., St-Onge M., Little K., Duplessis M., and Barabe F. J. Am. Chem. Soc. 129 (2007) 44
11. Satoh T., Kurihara T., and Fujita K. Tetrahedron 57 (2001) 5369
12. Satoh T., and Saito S. Tetrahedron Lett. 45 (2004) 347
13. Satoh T., Nagamoto S., Yajima M., Yamada Y., Ohata Y., and Tadokoro M. Tetrahedron Lett. 49 (2008) 5431
14. Satoh T., Noguchi T., and Miyagawa T. Tetrahedron Lett. 49 (2008) 5689
15. Satoh T., Miura M., Sakai K., and Yokoyama M. Tetrahedron 62 (2006) 4253
16. Preliminary results of this study were reported as a Letter. 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. Soai K., Oyamada H., Takase M., and Ookawa A. Bull. Chem. Soc. Jpn. 57 (1984) 1948
19. MuMurry J. Organic Chemistry. 3rd ed. (1992), Brooks/Cole Publishing Company, Belmont
20. Satoh T., Ogino Y., and Ando K. Tetrahedron 61 (2005) 10262
21. Some recent reviews concerning chemistry, synthesis, and synthetic uses of cyclopropanes:
22. Salaun J. Chem. Rev. 89 (1989) 1247
23. Sonawane H.R., Bellur N.S., Kulkarni D., and Ahuja J.R. Synlett (1993) 875
24. Hoveyda A.H., Evans D.A., and Fu G.C. Chem. Rev. 93 (1993) 1307
25. Doyle M.P., and Protopopova M.N. Tetrahedron 54 (1998) 7919
26. Donaldson W.A. Tetrahedron 57 (2001) 8589
27. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977
28. Pietruszka J. Chem. Rev. 103 (2003) 1051
29. Reissig H.-U., and Zimmer R. Chem. Rev. 103 (2003) 1151
30. Kulinkovich O.G. Chem. Rev. 103 (2003) 2597
31. Halton B., and Harvey J. Synlett (2006) 1975