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. 2003 Oct 15;125(41):12412-3.
doi: 10.1021/ja037086r.

Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity

Carolyn E Anderson  1 , Larry E Overman
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Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity

Carolyn E Anderson et al. J Am Chem Soc. .

Abstract

COP-Cl catalyzes the rearrangement of (E)-allylic trichloroacetimidates to provide transposed allylic trichloroacetamides of high enantiopurity, a transformation that underlies the first truly practical method for transforming prochiral allylic alcohols to enantioenriched allylic amines and congeners. The high functional group compatibility of this asymmetric rearrangement and the demonstrated broad utility in synthesis of the allylic trichloroacetimidate to allylic trichloroacetamide conversion are singular features of this new catalytic asymmetric reaction.

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