Overman rearrangement

The Overman rearrangement is a chemical reaction that can be described as a Claisen rearrangement of allylic alcohols to give allylic trichloroacetamides. The Overman rearrangement was discovered in 1974 by Larry Overman.



The [3,3]-sigmatropic rearrangement is diastereoselective and can be catalyzed by heat, Hg(II), or Pd(II). The resulting allylamine structures can be transformed into many chemically and biologically important natural and un-natural amino acids (like (1-adamantyl)glycine).

Further readings

 * Isobe, M. et al. Tetrahedron Lett. 1990, 31, 3327.
 * Allmendinger, T. et al. Tetrahedron Letters 1990, 31, 7301.
 * Nishikawa, T.; Asai, M.; Ohyabu, N.; Isobe, M.; J. Org. Chem. 1998, 63(1), 188-192. (PMID: 11674062)