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Catalytic Asymmetric Rearrangement of Allylic Trichloroacetimidates. A Practical Method for Preparing Allylic Amines and Congeners of High Enantiomeric Purity

2003/09/19 by Carolyn E. Anderson, Larry E. Overman · 2 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · #Chemical Synthesis and Analysis #Asymmetric Hydrogenation and Catalysis #Chemical Synthesis and Reactions

paper · doi:10.1021/ja037086r

openalex publication_date 2003/09/19 · openalex created_date 2025/10/10 · openalex updated_date 2026/06/26

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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