Medium-dependent lithiated side products in the reductive lithiation of allylic phenyl thioethers. Diethyl ether versus tetrahydrofuran

Tetrahedron Letters

Volumn 46, Issue 25, 2005, Pages 4357-4360

  Screttas, Constantinos G ^a   Heropoulos, Georgios A ^a   Micha Screttas, Maria ^a   Steele, Barry R ^a  

^a INSTITUTE OF BIOLOGY   (Greece)

Author keywords

Metalation; Organolithium; Reduction; Regioselectivity

Indexed keywords

ALLYL COMPOUND; BENZENE DERIVATIVE; ETHER DERIVATIVE; SULFIDE; TETRAHYDROFURAN;

ARTICLE; CHEMICAL REACTION; GAS CHROMATOGRAPHY; LITHIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; RING OPENING;

EID: 19444365357     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.080     Document Type: Article

References (23)

1. S. Streiff, N. Robeiro, and L.D. Désaubry Chem. Commun. 2004 346 347
2. C.G. Screttas, and M. Micha-Screttas J. Org. Chem. 43 1978 1064 1071
3. T. Cohen, W.M. Daniewski, and R.B. Weisenfeld Tetrahedron Lett. 1978 4665 4668
4. For reviews see: J. Clayden Organolithiums: Selectivity for Synthesis, Tetrahedron Organic Chemistry Series Vol. 23 2002 Chapter 4
5. D.J. Ramon, and M. Yus Eur. J. Org. Chem. 2000 225 237
6. M. Yus, R.P. Herrera, and A. Guijarro Chem. Eur. J. 8 2002 2574 2584
7. C.G. Screttas, and J.F. Eastham J. Am. Chem. Soc. 87 1965 3276 3277
8. C.G. Screttas, and I.C. Smonou J. Organomet. Chem. 342 1988 143 152
9. T. Fugita, K. Suga, and S. Watanabe Synthesis 1972 630
10. A. Maercker, and R.W. Stumpe Tetrahedron Lett. 1979 3843 3846
11. A. Maercker Angew. Chem., Int. Ed. Engl. 26 1987 972 989
12. P.D. Bartlett, C.W. Tauber, and W.P. Weber J. Am. Chem. Soc. 91 1969 6362 6366
13. L. Spialter, and C.W. Harris J. Org. Chem. 31 1966 4263 4264
14. C.G. Screttas, and M. Micha-Screttas J. Org. Chem. 48 1983 153 158
15. T. Cohen, and B.-S. Guo Tetrahedron 42 1986 2803 2808
16. B.-S. Guo, W. Doubleday, and T. Cohen J. Am. Chem. Soc. 109 1987 4710 4711
17. V. Kulkarni, and T. Cohen Tetrahedron 56 1997 12089 12100
18. C.G. Screttas, G.A. Heropoulos, M. Micha-Screttas, B.R. Steele, and D.P. Catsoulacos Tetrahedron Lett. 44 2003 5633 5635
19. T. Cohen, T. Kreethadumrongdat, X. Liu, and V.J. Kulkarni Am. Chem. Soc. 123 2001 3478 3483
20. J.J. Eisch, and A.M. Jacobs J. Org. Chem. 28 1963 2145 2146
21. Y. Yamamoto, H. Yatagai, and K. Maruyama J. Am. Chem. Soc. 103 1981 1969 1975
22. T. Fukuda, R. Irie, and T. Katsuki Tetrahedron 55 1999 649 664
23. Y. Morimoto, T. Iwai, and T. Kinoshita J. Am. Chem. Soc. 121 1999 6792 6797