Carroll rearrangement

[1] This organic reaction is accompanied by decarboxylation and the final product is a γ,δ-allylketone.

[2] With palladium(0) as a catalyst, the reaction (Tsuji, 1980) is much milder (path B) with an intermediate allyl cation / carboxylate organometallic complex.

[5] The first reported asymmetric rearrangement is catalyzed by tris(dibenzylideneacetone)dipalladium(0) and the Trost ligand:[4] A similar reaction[6] uses additional naphthol.

It remains to be seen if this reaction will have a wide scope because the acetamido group appears to be a prerequisite.

The same catalyst but a different ligand is employed in this enantioconvergent reaction:[7] The scope is extended to asymmetric α-alkylation of ketones masked as their enol carbonate esters:[8]