Novel Catalysts for the Overman Rearrangement

 

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Abstract

PtCl₂, PtCl₄, AuCl, and AuCl₃ were found to be efficient catalysts for the Overman rearrangement of O-allyltrichloroacetimidates to N-allyltrichloroacetamides.

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Introduction of an amino group at a tertiary carbon has been achieved using Hg(II)-catalyzed Overman rearrangement.^1a In our hands, imidate 1d with PdCl₂(PhCN)₂ also gave a very low yield of amide 2d due to competitive elimination of trichloroacetamide (4).