Chlorotrimethylsilane-mediated Michael addition reactions of chiral benzylic anions derived from η6-chromiumtricarbonyl complexes

Journal of Organometallic Chemistry

Volumn 658, Issue 1-2, 2002, Pages 21-33

  Beckwith, Rohan E J ^a   Heron, Nicola ^b   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

6 chromiumtricarbonyl; Asymmetric synthesis; Chiral lithium amide; Chlorotrimethylsilane; Michael addition

Indexed keywords

ANION; BENZILIC ACID DERIVATIVE; CHLOROTRIMETHYLSILANE; CHROMIUM DERIVATIVE; CYCLOHEXANONE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; METAL COMPLEX; ORGANOLITHIUM COMPOUND;

ARTICLE; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; CONTROLLED STUDY; DERIVATIZATION;

EID: 0037120201     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(02)01590-5     Document Type: Article

References (27)

1. 6-chromiumtricarbonyl complexes, see: M.F. Semmelhack, in: E.W. Abel, F.G.A. Stone, G. Wilkinson, L.S. Hegedus (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Elsevier Science Ltd, Oxford, 1995, p. 979.
2. M.F. Semmelhack, J.J. Harrison, Y. Thebtaranonth, J. Org. Chem. 44 (1979) 3275.
3. E.P. Kundig, H. Ratni, B. Crousse, G. Bernardinelli, J. Org. Chem. 66 (2001) 1852.
4. C.A. Merlic, J.C. Walsh, J. Org. Chem. 66 (2001) 2265.
5. (a) H.-G. Schmalz, S. Siegel, J.W. Bats, Angew. Chem. Int. Ed. Engl. 34 (1995) 2383;
6. (b) H.-G. Schmalz, S. Siegel, A. Schwarz, Tetrahedron Lett. 37 (1996) 2947;
7. (c) O. Hoffmann, H.-G. Schmalz, Synlett (1998) 1426.
8. 6-chromium-tricarbonyl complexes, see: (a) S.G. Davies, T.D. McCarthy, in: E.W. Abel, F.G.A. Stone, G. Wilkinson, L.S. Hegedus (Eds.), Comprehensive Organometallic Chemistry II, vol. 12, Elsevier Science Ltd, Oxford, 1995, p. 1039;
9. (b) S.G. Davies, S.J. Coote, C.L. Goodfellow, in: L.S. Liebeskind (Ed.), Advances in Metal-Organic Chemistry, vol. 2, JAI Press, Greenwich, CT, 1991, p. 1.
10. (a) A. Ariffin, A.J. Blake, R.A. Ewin, N.S. Simpkins, Tetrahedron: Asymmetry 9 (1998) 2563;
11. (b) A. Ariffin, A.J. Blake, R.A. Ewin, W.-S. Li, N.S. Simpkins, J. Chem. Soc. Perkin Trans. 1 (1999) 3177.
12. (a) E.L.M. Cowton, S.E. Gibson, M.J. Schnider, M.H. Smith, Chem. Commun. (1996) 839;
13. (b) S.E. Gibson, P. Ham, G.R. Jefferson, M.H. Smith, J. Chem. Soc. Perkin Trans. 1 (1997) 2161;
14. (c) S.E. Gibson, P. O'Brien, E. Rahimian, M.H. Smith, J. Chem. Soc. Perkin Trans. 1 (1999) 909;
15. (d) S.E. Gibson, P.C.V. Potter, M.H. Smith, Chem. Commun. (1996) 2757.
16. M.F. Semmelhack, Y. Thebtaranonth, L. Keller, J. Am. Chem. Soc. 99 (1977) 959.
17. J. Furukawa, N. Kawabata, Adv. Organomet. Chem. 12 (1974) 83.
18. (a) G.M. Rubottom, M.I. Lopez, J. Org. Chem. 38 (1973) 2097;
19. (b) I. Ryu, H. Suzuki, A. Ogawa, N. Kambe, N. Sonoda, Tetrahedron Lett. 29 (1988) 6137.
20. I. Ryu, K. Matsumoto, M. Ando, S. Murai, N. Sonoda, Tetrahedron Lett. 21 (1980) 4283.
21. See: C.A. Merlic, M.M. Miller, B.N. Hietbrink, K.N. Houk, J. Am. Chem. Soc. 123 (2001) 4904 (and references therein).
22. (a) K.I. Booker-Milburn, Synlett 4 (1992) 809;
23. (b) N. Iwasawa, M. Funahashi, S. Hayakawa, K. Narasaka, Chem. Lett. (1993) 545.
24. K.I. Booker-Milburn, A. Barker, W. Brailsford, B. Cox, T. Mansley, Tetrahedron 54 (1998) 15321.
25. Y. Ito, S. Fujii, M. Nakatsuka, F. Kawamoto, T. Saegusa, Org. Synth. Coll. 6 (1988) 327.
26. E.P. Kundig, D.P. Amurrio, G. Bernardinelli, R. Chowdhury, Organometallics 12 (1993) 4275.
27. M.J. Siwek, J.R. Green, Synlett (1996) 560.