Preparation of differentially 1,3-disubstituted indolines by intramolecular carbolithiation

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5303-5305

  Bailey, William F ^a   Luderer, Matthew R ^a   Mealy, Michael J ^b  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b H LUNDBECK A S   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

(1 LITHIO 3 INDOLINYL)METHYLLITHIUM; ANILINE DERIVATIVE; EPHEDRINE DERIVATIVE; ETHER DERIVATIVE; INDOLE DERIVATIVE; LITHIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOLITHIATION; CHEMICAL REACTION; CHROMATOGRAPHY; CYCLIZATION; ENANTIOSELECTIVITY; POLYMERIZATION; TEMPERATURE;

EID: 0038684459     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01204-8     Document Type: Article

References (14)

1. Bailey W.F., Jiang X.-L. J. Org. Chem. 61:1996;2596.
2. Zhang D., Liebeskind L.S. J. Org. Chem. 61:1996;2594.
3. Bailey W.F., Mealy M.J. J. Am. Chem. Soc. 122:2000;6787.
4. Gil G.S., Groth U.M. J. Am. Chem. Soc. 122:2000;6789.
5. Barluenga J., Perez-Prieto J., Asensio G. Tetrahedron. 46:1990;2453.
6. Yoshida Y., Tanabe Y. Synthesis. 1997;533.
7. On a molecular scale, deprotonation of 1 likely occurs more rapidly than does the exchange. For a detailed discussion of the relative rates of such processes in a related system, see: Gallagher D.J., Beak P. J. Am. Chem. Soc. 113:1991;7984.
8. 4), concentrated by rotary evaporation, and the residue was purified by flash chromatography on silica gel.
9. 15N 161.1204, found 161.1222.
10. Bailey W.F., Khanolkar A.D., Gavaskar K., Ovaska T.V., Rossi K., Thiel Y., Wiberg K.B. J. Am. Chem. Soc. 113:1991;5720.
11. Rölle T., Hoffmann R.W. J. Chem. Soc., Perkin Trans. 2. 1995;1953.
12. Coote S.J., Davies S.G., Goodfellow C.L., Sutton K.H., Middlemiss D., Naylor A. Tetrahedron: Asymmetry. 1:1990;817.
13. Wiberg K.B., Bailey W.F. J. Mol. Struct. 556:2000;2.
14. It might be noted that we have not attempted to optimize the enantioselectivity of the cyclization by modification of the pseudoephedrine-derived ligand.