Catalytic asymmetric rearrangement of allylic trichloroacetimidates. A practical method for preparing allylic amines and congeners of high enantiomeric purity.
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.
Anderson
Carolyn E
CE
Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.
Overman
Larry E
LE
D000081:Acetamides; D000498:Allyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis*; D062845:Chloroacetates; D013237:Stereoisomerism; D014238:Trichloroacetic Acid / Q000737:chemistry*
D000081:Acetamides; D000498:Allyl Compounds; D000588:Amines; D062845:Chloroacetates; D014238:Trichloroacetic Acid; C009528:trichloroacetamide