Indium(I) bromide-promoted stereoselective preparation of cyclopropanes via sequential aldol-type coupling/elimination/Michael-induced ring closure reaction from α,α-dichloroacetophenone and aldehydes

Journal of Organometallic Chemistry

Volumn 693, Issue 21-22, 2008, Pages 3441-3445

  Peppe, Clovis ^a   das Chagas, Rafael Pavão ^a   Burrow, Robert Alan ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Aldol type coupling; Elimination reaction; Indium(I); Michael induced ring closure reaction; Sequential chemical reactions

Indexed keywords

ALDEHYDES; KETONES; ORGANIC COMPOUNDS; PROPANE;

ALDOL-TYPE COUPLING; ELIMINATION REACTION; ENOLATE; INDIUM(I); MICHAEL-INDUCED RING CLOSURE REACTION; REACTION MECHANISMS; RING CLOSURE REACTIONS; SEQUENTIAL CHEMICAL REACTIONS; STEREOSELECTIVE PREPARATION;

INDIUM;

EID: 52049110520     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2008.08.011     Document Type: Article

References (20)

1. For a discussion on the oxidative insertion reactions of indium(I) compounds see:. Peppe C. Curr. Org. Synth. 1 (2004) 227
2. Peppe C., and das Chagas R.P. Synlett (2004) 1187
3. Peppe C., and das Chagas R.P. Synlett (2006) 605
4. Nóbrega J.A., Gonçalves S.M.C., and Peppe C. Tetrahedron Lett. 41 (2000) 5779
5. Nóbrega J.A., Gonçalves S.M.C., and Peppe C. Tetrahedron Lett. 42 (2001) 4745
6. For 1a see:. Peppe C., and das Chagas R.P. J. Organomet. Chem. 691 (2006) 5856
7. For 1b see:. Peppe C., Mello P.D., and das Chagas R.P. J. Organomet. Chem. 691 (2006) 2335
8. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., and Hudlicky T. Chem. Rev. 89 (1989) 165
9. Donaldson W.A. Tetrahedron 57 (2001) 8589
10. Taylor R.E., Engelhardt F.C., and Schmitt M.J. Tetrahedron 59 (2003) 5623
11. Li A.-H., Dai L.-X., and Aggarwal V.K. Chem. Rev. 97 (1997) 2341
12. For a discussion about the stereoselective preparation of cyclopropanes see:. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977
13. Pellissier H. Tetrahedron 64 (2008) 7041
14. Deb M.L., and Bhuyan P.J. Tetrahedron Lett. 46 (2005) 6453
15. Bigi F., Conforti M.L., Maggi R., Piccinno A., and Sartori G. Green Chem. 2 (2000) 101
16. DiBiase S.A., Lipisko B.A., Haag A., Wolak R.A., and Gokel G.W. J. Org. Chem. 44 (1979) 4640
17. Matano Y. J. Chem. Soc., Perkin Trans. 1 (1994) 2703
18. Hetschko M., and Gosselck J. Chem. Ber. 106 (1973) 996
19. Ren Z., Cao W., Ding W., and Wang Y. Synthesis (2005) 2718
20. Kojima S., Suzuki M., Watanabe A., and Ohkata K. Tetrahedron Lett. 47 (2006) 9061