Overman rearrangement

The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides through an imidate intermediate.^[1][2][3] The Overman rearrangement was discovered in 1974 by Larry Overman.^[4]

The Overman rearrangement

The [3,3]-sigmatropic rearrangement is diastereoselective and requires heating or the use of Hg(II) or Pd(II) salts as catalysts.^[5] The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids (like (1-adamantyl)glycine).^[6]

The Overman rearrangement may also be used for asymmetric synthesis.^[7][8]

See also

• Pinner reaction