(Trimethylsilyl)cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings

Journal of the American Chemical Society

Volumn 103, Issue 6, 1981, Pages 1604-1606

  Danheiser, Rick L ^a   Carini, David J ^a   Basak, Ajoy ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007930541     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00396a071     Document Type: Article

References (11)

1. For a review of electrophilic substitution of organosilicon compounds, see: Chan, T. H.; Fleming, I. Synthesis 1979, 761.
2. Danheiser, R. L.; Carini, D. J. J. Org. Chem. 1980, 45, 3925.
3. Bourgeois, P.; Calas, R.; Merault, G. J. Organomet. Chem. 1977, 141, 23. Bourgeois, P. C. R. Hebd. Seances Acad. Sci., Ser. C. 1974, 278, 969.
4. Jellal, A.; Santelli, M. Tetrahedron Lett. 1980, 4487.
5. The C-Si bond in (trimethylsilyl)allenes is oriented cis coplanar to only the allylic ir bond and thus can only afford direct stabilization to the transition state resulting from electrophilic substitution at C3.
6. For a review of 1,2-cationic rearrangements in organosilicon compounds, see: Brook, A. G.; Bassindale, A. R. In “Rearrangements in Ground and Excited States”; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. II, pp 190-192.
7. For a review of migration across the double bond of vinyl cations, see: Stang, P. J.; Rappaport, Z.; Hanack, M.; Subramanian, L. R. “Vinyl Cations”; Academic Press: New York, 1979; pp 459-483.
8. Westmijze, H.; Vermeer, P. Synthesis 1979, 390. We thank James T. Kadonaga for assistance in the preparation of these alienes.
9. For a review of the chemistry of vinylsilanes, see: Fleming, I. In “Comprehensive Organic Chemistry”; Jones, D. N., Ed.; Pergamon Press: Oxford, 1979; Vol. 3, pp 608-662.
10. This assignment assumes antiparallel approach of aliene from the less hindered face of the alkoxy a Hylic carbocation; Siscovic, E.; Rao, A. S. Curr. Sci. 1968, 37, 286.
11. Whitesell, J. K.; Matthews, R. S. J. Org. Chem. 1977, 42, 3878.