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Keywords:

  • alkene geometry;
  • alkynes;
  • stereoselectivity;
  • halosilylation;
  • migration
Thumbnail image of graphical abstract

Migrating through Si valley: The highly stereoselective formation of α-silyl-β- haloenones by way of silicon group migration is described. Electrophilic activation of the alkyne by N-halosuccinimides induced an anti-selective migration to give highly substituted enones (see scheme). These enone products can be readily converted to the all-carbon tetrasubstituted alkenes while maintaining their geometry.