Tritylallyldimethylsilane - TiCl4 annulations to electron deficient olefins. Diastereomerically pure 3-substituted and 3,4-disubstituted cyclopentanols

Journal of Organic Chemistry

Volumn 61, Issue 10, 1996, Pages 3230-3231

  Brengel, Gregory P ^a   Meyers, A I ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000890707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601021     Document Type: Article

References (24)

1. (a) Danheiser, R. L.; Dixon, B. R.; Gleason, R. W. J. Org. Chem. 1992, 57, 6094.
2. (b) Danheiser, R. L.; Takahashi, T.; Bertok, B.; Dixon, B. R. Tetrahedron Lett. 1993, 34, 3845.
3. (c) Knolker, H-J.; Foitzik, N.; Goesmann, H.; Graf, R. Angew. Chem., Int. Ed. Engl. 1993, 32, 1081.
4. (d) Knolker, H.-J.; Foitzik, N.; Graf, R.; Pannek, J.-B. Tetrahedron 1993, 49, 9955.
5. (e) Knolker, H.-J.; Graf, R. Tetrahedron Lett. 1993, 34, 4765.
6. (f) Knolker, H.-J.; Graf, R. Synlett. 1994, 131 and references cited therein.
7. (g) Knolker, H.-J.; Baum, G.; Graf, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1612 and references cited therein.
8. (h) Monti, H.; Audran, G.; Monti, J.-P.; Leandri, G. Synlett 1994, 403 and references cited therein.
9. (i) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345. Hosomi, A. Tetrahedron Lett. 1993, 34, 8123.
10. (i) Panek, J. S.; Jain, N. F. J. Org. Chem. 1993, 58, 2345. Hosomi, A. Tetrahedron Lett. 1993, 34, 8123.
11. (j) Brengel, G. P.; Rithner, C.; Meyers, A. I. J. Org. Chem. 1994, 59, 5144 and references cited therein.
12. Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
13. Tamao, K.; Ishida, N. J. Organomet. Chem. 1984, 269, C37.
14. Fleming, I.; Henning, R.; Parker, D. C.; Plaut, H. E.; Sanderson, P. E. J. J. Chem. Soc., Perkin Trans. 1 1995, 317 and references cited therein.
15. Review: Hosomi, A. Acc. Chem. Res. 1988, 21, 200.
16. Knölker, H.-J.; Wanzyl, G. Synlett 1995, 378.
17. Mayr, H.; Patz, M. Angew. Chem., Int. Ed. Engl. 1994, 33, 938. The phenyl groups act as electron-withdrawing substituents and significantly reduce the reactivity of the allyl group.
18. Ager, D. J.; Fleming, I. J. Chem. Res. (S) 1977, 6.
19. 13C NMR) obtained for bicyclic keto alcohol 9 compare well with those reported by Knölker (see reference 6).
20. The full scope of cycloaddition reactions with 6, including the formation and utilization of tricyclic lactams i and ii, will be the subject of a future publication. (Matrix Presented)
21. 2O).
22. Commercially available tetrabutylammonium fluoride (1.0 M in THF) can be sufficiently dried immediately prior to use by stirring 2-3 h over 3 Å sieves.
23. Anhydrous cesium fluoride is prepared by heating the solid in the reaction vessel, under vacuum, with a heat gun for several minutes.
24. 1H NMR spectrum. Careful examination of the protons at the hydroxy carbons (≈4.3-4.4 ppm) in 13 showed <3% of the epimers 14.