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Paper | Special issue | Vol 59, No. 1, 2003, pp.137-147
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S6
The First Example of an Amide-Carbonyl Stabilized Oxiranyl Anion: Generation from Epoxysilane, Its Properties, and Trapping with Electrophiles

Tsuyoshi Satoh,* Takayuki Shimura, and Ken Sakai

*Department of Chemistry, Faculty of Science, Science University of Tokyo, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan


An epoxysilane having an amide group at the α-carbon was synthesized from phenylacetylene. An amide-carbonyl stabilized oxiranyl-ammonium was generated from the epoxysilane in THF with tetrabutylammonium fluoride (TBAF). The generated oxiranyl anion was found to have enough nucleophilicity with aldehydes to give moderate to good yields of the adducts. In some reactions, the oxiranylammonium was found to be configurationally unstable to give the epimers.