Formation of α-dialkylamino alkyllithium intermediates in the reaction of N,N-dialkylamides with PhMe2SiLi followed by a second lithium reagent, and their alkylation, fragmentation, cyclisation and rearrangement by proton transfer

Chemical Communications

Volumn , Issue 6, 1998, Pages 715-716

  Fleming, Ian ^a   Mack, Stephen R ^a   Clark, Barry P ^b  

^a Department of Chemistry ^*  (United Kingdom)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002285931     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a800651b     Document Type: Article

References (15)

1. I. Fleming, S. R. Mack and B. P. Clark, Chem. Commun., 1998, 713.
2. I. Coldham and R. Hufton, Tetrahedron Lett., 1995, 36, 2157 and references cited therein.
3. K. Tamao, T. Yamauchi and Y. Ito, Chem. Lett., 1987, 171;
4. I. Fleming, Pure Appl. Chem., 1990, 62, 1879;
5. P. F. Hudrlik, Y. M. Abdallah and A. M. Hudrlik, Tetrahedron Lett., 1992, 33, 6747;
6. M. Murakami, M. Suginome, K. Fujimoto, H. Nakamura, P. G. Andersen and Y. Ito, J. Am. Chem. Soc., 1993, 115, 6487;
7. S. C. Archibald and I. Fleming, Tetrahedron Lett., 1993, 34, 2387;
8. A. Barbero, D. C. Blakemore, I. Fleming and R. N. Wesley, J. Chem. Soc., Perkin Trans, 1, 1997, 1329.
9. H. Gilman, R. A. Benkeser and G. E. Dunn, J. Am. Chem. Soc., 1950, 72, 1689;
10. S. M. Sieburth and L. Fensterbank, J. Org. Chem., 1993, 58, 6314;
11. J. G. Duboudin, B. Jousseaume and M. Pinet-Vallier, J. Organomet. Chem., 1979, 172, 1.
12. S. Bank, A. Schriesheim and C. A. Rowe, J. Am. Chem. Soc., 1965, 87, 3244;
13. D. A. Hutchinson, K. R. Beck, R. A. Benkeser and J. B. Grutzner, J. Am. Chem. Soc., 1972, 95, 7075;
14. R. A. Benkeser, Synthesis, 1971, 347;
15. M. Schlosser, J. Hartmann and V. David, Helv. Chim. Acta, 1974, 57, 1567.