Abstract
AbstractThe first small anion‐triggered Steglich rearrangements are reported. Tetrabutylammonium carboxylates‐, cyanide‐ and fluoride promote the O‐ to C‐acyl transfer of a range of O‐acylated oxindoles to form 3,3‐disubstituted oxindole products with new quaternary stereocentres. DFT calculations on the TBAF‐mediated reaction strongly support a nucleophilic catalysis mechanism involving initial attack of fluoride on the O‐acyl group to give an enolate and an acyl fluoride in the rate determining step.
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