COP-Cl Catalyst

chemfiles volume 5 article 4

Allylic imidate rearrangements are the preferred method for converting readily available allylic alcohols to transposed allylic amines and their analogues. Overman recently employed a cationic palladium catalyst in an asymmetric version of this rearrangement. A set of (E)-allylic trichloroacetimidates provided transposed allylic trichloroacetamides in high yields and enantioselectivities (up to 98% ee), whereas the (Z)-allylic imidates showed slightly reduced selectivities (Scheme 2).1

Scheme 2

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  1. Anderson, C. E.; Overman, L. E. J. Am. Chem. Soc. 2003, 125, 12412.

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