Reaction of silyl-substituted carbanions with functionalized oxiranes will be exploited in a domino process involving a series of nucleophilic substitution reactions and a silicon migration to give novel ring compounds with potential biological activity

• Applicant: Professor Dr. Ernst Schaumann
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2006 to 2009
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 26477264

• Final Report Year: 2008

Final Report Abstract

The various facets of domino reactions involving a silyl shift as key step have been compiled in two reviews.[1,2] This material is not duplicated here. However, it was found that silyl oxiranes display an ambiphilic reactivity toward silyl-substituted carbanions.[3] The reactions of these anions with tris-electrophiles have so far not allowed to isolate an annulation products Carboxylates were tested instead of epoxides as nucleophilic reaction component.[6]

Publications

• A. Kirschning, C. Kujat, S. Luiken, E. Schaumann, Eur. J. Org. Chem. 2007, 2387.
  
  
• E. Schaumann, A. Kirschning, Synlett 2007, 177.
  
  
• E. Schaumann, T. Puschke, J. Lange, Tetrahedron Lett. 2008, 49, 2628.