Improved addition of organolithium reagents to hindered and/or enolisable ketones

Tetrahedron

Volumn 59, Issue 12, 2003, Pages 2169-2176

  Lecomte, Vincent ^a   Stéphan, Elie ^a   Le Bideau, Franck ^a   Jaouen, Gérard ^a  

^a CNRS   (France)

Author keywords

Addition reaction; Ketones; Lithium and compounds; Steroid

Indexed keywords

KETONE DERIVATIVE; ORGANOLITHIUM COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; STEROID; TESTOSTERONE;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PRECURSOR; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; TEMPERATURE;

EID: 0037450996     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00189-3     Document Type: Article

References (34)

1. Reetz M.T., Westermann J., Steinbach R., Peter R., Ostarek R., Maus S. Chem. Ber. 118:1985;1421-1440.
2. Imamoto T. Pure Appl. Chem. 62:1990;747-752.
3. Stéphan E., Affergan T., Weber P., Jaouen G. Tetrahedron Lett. 39:1998;9427-9430.
4. Lecomte V., Stéphan E., Jaouen G. Tetrahedron Lett. 43:2002;3463-3465.
5. Lecomte V., Foy N., LeBideau F., Stéphan E., Jaouen G. Tetrahedron Lett. 42:2001;5409-5411.
6. Ashby E.C., Laemmle J.T. Chem. Rev. 75:1975;521-546.
7. Dimitrov V., Bratovanov S., Simova S., Kostova K. Tetrahedron Lett. 35:1994;6713-6716.
8. (a) Pallaud R., Pleau J. C. R. Acad. Sci. Paris. 265:1967;1479-1482
9. (b) Coxon J.M., Steel P.J. Aust. J. Chem. 32:1979;2441-2453.
10. Kozlov N.G., Popova L.A., Vyalimyae T.K., Knizhnikov V.A., Ol'dekop Y.A. J. Org. Chem. USSR (Engl. Transl.). 25:1989;702-705.
11. Fonken G.S. J. Org. Chem. 30:1965;2095-2096.
12. Buhler J.D. J. Org. Chem. 38:1973;904-906.
13. Panev S., Dimitrov V. Tetrahedron: Asymmetry. 11:2000;1517-1526.
14. Landor S.R., O'Connor P.W., Tatchell A.R., Balir I. J. Chem. Soc., Perkin Trans. 1. 1973;473-478.
15. House H.O., Czuba L.J., Gall M., Olmstead H.D. J. Org. Chem. 34:1969;2324-2333.
16. (a) Benkeser R.A., Siklosi M.P., Mozdzen E.C. J. Am. Chem. Soc. 100:1978;2134-2139
17. (b) Benkeser R.A., Broxterman W.E. J. Am. Chem. Soc. 91:1969;5162-5163.
18. (a) Gérard F., Miginiac P. C. R. Acad. Sci. Paris. 275:1972;1129-1131
19. (b) Barbot F., Miginiac P. Bull. Soc. Chim. Fr. 1977;113-116.
20. Chastrette M., Amouroux R. Bull. Soc. Chim. Fr. 12:1970;4348-4353.
21. Ashby E.G., Noding S.A. J. Org. Chem. 44:1979;4371-4377.
22. (a) Jackman L.M., Scarmoutzos L.M. J. Am. Chem. Soc. 106:1984;4627-4629
23. (b) Bauer W., Winchester W.R., Schleyer P.R. Organometallics. 6:1987;2371-2379.
24. McGarrity J.F., Ogle C.A. J. Am. Chem. Soc. 107:1985;1805-1810.
25. McKeever L.D., Waack R., Doran M.A., Baker E.B. J. Am. Chem. Soc. 91:1969;1057-1061.
26. Al-Aseer M.A., Smith S.G. J. Org. Chem. 49:1984;2608-2613.
27. Smith S.G., Charbonneau L.F., Nowak D.P., Brown T.L. J. Am. Chem. Soc. 94:1972;7059-7063.
28. Still W.C., Khan M., Mitra A.J. J. Org. Chem. 43:1978;2923-2925.
29. Bernstein S., Littell R., Williams J.H. J. Am. Chem. Soc. 75:1953;1481-1482.
30. Coxon J.M., Steel P.J. Aust. J. Chem. 32:1979;2441-2453.
31. (a) Bergdahl M., Vilsson M., Olsson T., Stern K. Tetrahedron. 47:1991;9691-9702
32. (b) Coxon J.M., Steel P.J., Coddington J.M., Rae I.D., Jones A.J. Aust. J. Chem. 31:1978;1223-1233.
33. Manoharan M., Eliel E.L. J. Am. Chem. Soc. 106:1984;367-372.
34. Zderic J.A., Batres E., Chávez Limón D., Carpio H., Lisci J., Monroy G., Necoechea E., Ringold H.J. J. Am. Chem. Soc. 82:1960;3404-3409.