Highly efficient gold(I)-catalyzed Overman rearrangement in water

• Dong Xing and
• Dan Yang

Beilstein J. Org. Chem. 2011, 7, 781–785, doi:10.3762/bjoc.7.88

• Dong Xing Dan Yang Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China 10.3762/bjoc.7.88 Abstract A highly efficient gold(I)-catalyzed Overman rearrangement of allylic trichloroacetimidates to allylic trichloroacetamides in water is reported. With this

• environmentally benign and scalable protocol, a series of C3-alkyl substituted allylic trichloroacetamides were synthesized in good to high yields. Keywords: allylic trichloroacetamides; allylic trichloroacetimidate; gold(I) chloride; Overman rearrangement; water; Introduction The aza-Claisen rearrangement of

• allylic trichloroacetimidates to allylic trichloroacetamides (Overman rearrangement) is a powerful and attractive strategy for the synthesis of allylic amines from readily available allylic alcohols [1][2]. This transformation can be conducted thermally at high temperatures or by transition metal