title: Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines.
abstract: The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral α,α-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium catalyst. The method allows for the formation of α,α-disubstituted allylic N-arylamines in moderate to good yields with good to excellent levels of regio- and enantioselectivity.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, 52242, United States.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Arnold
authors.forename: Hien M
authors.initials: HM
authors.lastname: Nguyen
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000498:Allyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D000586:Amination; D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D007700:Kinetics; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000081:Acetamides; D000498:Allyl Compounds; D000588:Amines; D000814:Aniline Compounds; D062845:Chloroacetates; D012238:Rhodium; C009528:trichloroacetamide; C023650:aniline