Overman Rearrangement

The Overman Rearrangement involves the conversion of allylic alcohols into allylic amines in two-steps via the rearrangement of an allylic trichloroacetimidate to an allylic trichloroacetamide.

Mechanism:

Literature:

Mumm, O.; Moller, F. Ber. 1937, 708, 2214.

Thermal and mercuric ion catalyzed [3,3]-sigmatropic rearrangement of allylic trichloroacetimidates. 1,3 Transposition of alcohol and amine functions. Overman, L.E.; J. Am. Chem. Soc. 1974, 96, 579.

A general method for the synthesis of amines by the rearrangement of allylic trichloroacetimidates. 1,3 Transposition of alcohol and amine functions. Overman, L.E.; J. Am. Chem. Soc. 1976, 98, 2901.

Allylic and propargylic imidic esters in organic synthesis. Larry E. Overman

Acc. Chem. Res., 1980, 13 (7), pp 218–224.

Mercury(II)- and Palladium(II)-Catalyzed [3,3]-Sigmatropic Rearrangements.

Overman, L.E.; Angew. Chem. Int. Ed. Engl. 1984, 23, 579.