Intramolecular carbolithiation of N-allyl-N-2-lithioallylamines: Effect of the allyl moiety

Comptes Rendus Chimie

Volumn 7, Issue 8-9, 2004, Pages 855-864

  Barluenga, José ^a   Fañnás, Francisco J ^a   Sanz, Roberto ^b   Fernández, Yolanda ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF BURGOS   (Spain)

Author keywords

Carbolithiation; Hexahydroindoles; Organolithium compounds; Pyrrolidines

Indexed keywords

ALLYL COMPOUND; ALLYLAMINE DERIVATIVE; BROMINE; INDOLE DERIVATIVE; LITHIUM; ORGANOLITHIUM COMPOUND; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; LITHIATION; METHODOLOGY; MOLECULAR INTERACTION; SYNTHESIS;

EID: 4444353880     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2004.02.015     Document Type: Article

References (21)

1. Bailey W.F. Patricia J.J. Del Globo V.C. Jarret R.M. Okarma P.J. J. Org. Chem. 50 1985 1999
2. Bailey W.F. Ovaska T.V. Advances in Detailed Reaction Mechanisms Coxon J.M. Mechanisms of Importance in Synthesis 3 1994 JAI Press Greenwich, CT 251
3. Mealy M.J. Bailey W.F. J. Organomet. Chem. 646 2002 59
4. Bailey W.F. Gavaskar K.V. Tetrahedron 50 1994 5957
5. Broka C.A. Lee W.J. Shen T. J. Org. Chem. 53 1988 1338
6. Broka C.A. Shen T. J. Am. Chem. Soc. 111 1989 2981
7. Coldham I. Hufton R. Tetrahedron Lett. 36 1995 2157
8. Zhang D. Liebeskind L.S. J. Org. Chem. 61 1996 2594
9. Bailey W.F. Jiang X.-L. J. Org. Chem. 61 1996 2596
10. Barluenga J. Sanz R. Granados A. Fañanás F.J. J. Am. Chem. Soc. 120 1998 4865
11. Bailey W.F. Mealy M.J. J. Am. Chem. Soc. 122 2000 6787
12. Sanz Gil G. Groth U.M. J. Am. Chem. Soc. 122 2000 6789
13. Barluenga J. Sanz R. Fañanás F.J. Tetrahedron Lett. 38 1997 2763
14. Fañanás F.J. Granados A. Sanz R. Ignacio J.M. Barluenga J. Chem. Eur. J. 7 2001 2896
15. Barluenga J. Fañanás F.J. Sanz R. Marcos C. Org. Lett. 4 2002 2225
16. Barluenga J. Fañanás F.J. Foubelo F. Yus M. J. Chem. Soc., Chem. Commun. 1988 1135
17. Woltering M.J. Fröhlich R. Hoppe D. Angew. Chem. Int. Ed. Engl. 36 1997 1764
18. Hoffmann R.W. Koberstein R. Remacle B. Krief A. Chem. Commun. 1997 2189
19. Hoffmann R.W. Koberstein R. Harms K. J. Chem. Soc., Perkin. Trans. 2 1999 183
20. 1,6-Dibromocyclohexene was prepared according to: J. Sonnenberg, S. Winstein J. Org. Chem 27 1962 748
21. Chamberlin A.R. Bloom S.H. Cervini L.A. Fotsch C.H. J. Am. Chem. Soc. 110 1988 4788