Danheiser annulation explained

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 . A. Basak . J. Am. Chem. Soc.. 1981. 103. 1604. 10.1021/ja00396a071. 6.
  2. Scope and Stereochemical Course of the (Trimethylsilyl)cyclopentene Annulation. R. L. Danheiser. Rick L. Danheiser. D. J. Carini . D. M. Fink . A. Basak . Tetrahedron. 1983. 39. 935. 10.1016/S0040-4020(01)88592-6. 6.
  3. The Reaction of Allenysilanes with α,β-Unsaturated Acylsilanes: New Annulation Approaches to Five and Six-Membered Carbocyclic Compounds. R. L. Danheiser . D. M. Fink . Tetrahedron Letters. 1985. 26. 2513. 10.1016/S0040-4039(00)98824-5. 21.
  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 . Y. -M. Tsai . Organic Syntheses. 1988. 66. 8. 10.15227/orgsyn.066.0008.
  5. Book: Organic Syntheses Based on Name Reactions. Alfred Hassner . C. Stumer . Elsevier. 2002. 008043259X.
  6. Book: Name Reactions: A Collection of Detailed Reaction Mechanisms. Jie Jack Li. Springer. 102. 2003. 3540402039.

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