Overman rearrangement

The Overman rearrangement represents a special form of the Claisen rearrangement of allyl alcohol with a dar. Here Trichloroacetonitrile is converted to the trichloroacetimidate. This then superimposed into a Claisen rearrangement to allylic trichloroacetamidate. The reaction is named after its discoverer, the American chemist Larry E. Overman (* 1943).

The [3,3 ] sigmatropic rearrangement is a diastereoselective rearrangement and in the presence of heat and a catalytic amount of mercury (II ) - performed or palladium ( II ) salts. The thus obtained allyl compounds can be used for the production of biologically important compounds and non- natural amino acids. The Overman rearrangement can be catalyzed enantioselectively using a chiral auxiliary.