Synthesis of Optically Active Arylcyclopentanes by Carbocyclisation of ω-Alkenylbenzyllithiums Involving Diastereofacial Differentiation

Synlett

Volumn 1996, Issue 10, 1996, Pages 1007-1009

  Krief, Alain ^a   Bousbaa, Jamal ^a  

^a UNIVERSITY OF NAMUR   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007884867     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5634     Document Type: Article

References (20)

1. Krief, A.; Barbeaux, P. J. Chem. Soc. Chem. Commun. 1987, 16, 1214.
2. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417.
3. Krief, A.; Hobe, M. Synlett 1992, 4, 317.
4. Van Ende, D.; Cravador, A.; Krief, A. J. Orgomet. Chem. 1979, 177, 1.
5. (a) Kato, T.; Marumoto, S.; Sato, T.; Kuwajima, I. Synlett, 1990, 671
6. (b) Krief, A.; Hobe, M. Tetrahedron Lett. 1992, 33, 6527
7. (c) Klein, S.; Marek, I.; Normant, J.-F. J. Org. Chem. 1994, 59, 2925.
8. (a) Keys, B.A.; Eliel, E.L.; Juaristi, E. Isr. J. Chem. 1989, 29, 171
9. (b) Krief, A.; Hobe, M., Dumont, W.; Badaoui, E.; Guittet, E.; Evrard, G. Tetrahedron Lett. 1992, 33, 3381
10. (c) Hoffmann, R.W., Rühl, T., Chemla, F.; Zahnheisen, T. Liebigs Ann. 1992, 719
11. (c) Fraenkel, G.; Martin, K.V. J. Amer. Chem. Soc. 1995, 117, 10336
12. (d) Ahlbrecht, H.; Harbach, J.; Hoffmann, R.W., Ruhland, T. Liebigs Ann. 1995, 211.
13. Bailey has already shown that t-BulLi undergoes exchange with a primary iodide more rapidly than it abstracts a proton from methanol: Bailey, W.F.; Patricia, J.J. Organomet. Chem. 1988, 352, 1.
14. 3: (a)11*, 26.9, 3, (b) 13*, 30.4, 3 (c) 6a*, 21.0, 2.6 (d) 16a*, -36.7, 2.35 (e) 19a*, 212.3, 2.
15. DAICEL CHIRACEL OD-H, cellulose carbamate phase supported on 5μm silica-gel, hexane : 2-propanol, 9:1, 0.5 ml/ mn, UV detector 220 nm. Retention time of ketones 16a′*/ 16a″*/ 16b′*/ 16b″* are 12.21/ 11.33/ 10.95/ 11.66 mn respectively.
16. The structures of 13b′* and 13b″* might be interchanged and it is also the case of 16b′* and 16b″*. We are working towards this end.
17. 9 the compounds 6* and 16* obtained from 2(S)-13* with those derived from racemic 2(R, S)-13.
18. Prochrom column, silicagel Merck 15.111, 15-40 mesh
19. (a) Nakamura, E. Pure Appl. Chem. 1996, 68, 123
20. (b) Klein, S.; Marek, I.; Poisson, J.-F.; Normant, J.-F. J. Am. Chem. Soc. 1995, 117, 8853.