Danheiser annulation

The Danheiser annulation or Danheiser TMS-cyclopentene annulation is an organic reaction of an α,β-unsaturated ketone and a trialkylsilylallene (e.g., trimethylsilyl- or triisopropylsilyl-) in the presence of a Lewis Acid to give a trialkylsilylcyclopentene in a regiocontrolled annulation. ^{[1][2][3][4][5][6]}

References

1. ^ "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.
2. ^ "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.
3. ^ "The Reaction of Allenysilanes with α,β-Unsaturated Acylsilanes: New Annulation Approaches to Five and Six-Membered Carbocyclic Compounds", R. L. Danheiser and D. M. Fink, Tetrahedron Lett. 1985, 26, 2513.
4. ^ "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.
5. ^ "Organic Syntheses Based on Name Reactions", By Alfred Hassner and C. Stumer, Elsevier, p. 78, 2002
6. ^ "Name Reactions: A Collection of Detailed Reaction Mechanisms", By Jie Jack Li, Springer, p. 102, 2003