[3 + 2] Annulation Methods Based on Organosilanes
Our laboratory has pioneered the application of allenylsilanes, propargylsilanes, and allylsilanes as three-carbon units in [3 + 2] annulation routes to a variety of five-membered carbocyclic and heterocyclic systems. This reaction, sometimes referred to as the "Danheiser Annulation", was selected for the cover of Hassner and Stumer's monograph on "Organic Syntheses Based on Name Reactions and Unnamed Reactions."
A number of variants of this [3 + 2] annulation strategy have been developed in our laboratory:
[3 + 2] Cyclopentene Annulation
"TMS-Cyclopentene Annulation: A Regiocontrolled Approach to the Synthesis of Five-Membered Rings", R. L. Danheiser, D. J. Carini, and A. Basak, J. Am. Chem. Soc.1981, 103, 1604.
"Scope and Stereochemical Course of the (Trimethylsilyl)cyclopentene Annulation", R. L. Danheiser, D. J. Carini, D. M. Fink, and A. Basak, Tetrahedron 1983, 39, 935.
"The Reaction of Allenysilanes with a,b-Unsaturated Acylsilanes: New Annulation Approaches to Five and Six-Membered Carbocyclic Compounds", R. L. Danheiser and D. M. Fink, Tetrahedron Lett. 1985, 26, 2513.
"A General [3+2] Annulation: cis-4-Exo-isopropenyl-1,9-dimethyl-8-(trimethylsilyl)bicyclo-[4.3.0]non-8-en-2-one", R. L. Danheiser, D. M. Fink, and Y. -M. Tsai, Organic Syntheses 1988, 66, 8.
[3 + 2] Annulation Route to Azulenes
"A New Synthesis of Substituted Azulenes", D. A. Becker and R. L. Danheiser, J. Am. Chem. Soc. 1989, 111, 389.
[3 + 2] Annulation Route to Five-Membered Oxygen and Nitrogen Heterocycles
"Application of Allenylsilanes in [3 + 2] Annulation Approaches to Five-Membered Oxygen and Nitrogen Heterocycles", R. L. Danheiser, C. A. Kwasigroch, and Y. -M. Tsai, J. Am. Chem. Soc.1985, 107, 7233.
[3 + 2] Annulation Route to Furans
"A New Synthesis of Substituted Furans", R. L. Danheiser, E. J. Stoner, H. Koyama, D. S. Yamashita, and C. A. Klade, J. Am. Chem. Soc.1989, 111, 4407.
[3 + 2] Annulation Route to Isoxazoles
"Application of Allenylsilanes in a Regiocontrolled [3 + 2] Annulation Route to Substituted Isoxazoles", R. L. Danheiser and D. A. Becker, Heterocycles 1987, 25, 277.
[3 + 2] Annulation Methods Based on Allylsilanes and Propargylsilanes
"Five-Membered Ring Annulation via Propargyl- and Allylsilanes", R. L. Danheiser, B. R. Dixon, and R. W. Gleason, J. Org. Chem. 1992, 57, 6094.
"Stereochemical Course of the Allylsilane Based Cyclopentane Annulation", R. L. Danheiser, T. Takahashi, Bila Bertsk, and B. R. Dixon, Tetrahedron Lett. 1993, 34, 3845.
Send mail to email@example.com questions
or comments about this web site.