title: Rhodium-catalyzed regio- and enantioselective amination of racemic secondary allylic trichloroacetimidates with N-methyl anilines.
abstract: We report the chiral diene ligated rhodium-catalyzed dynamic kinetic asymmetric transformation (DYKAT) of racemic secondary allylic trichloroacetimidates with a variety of N-methyl anilines, providing allylic N-methyl arylamines in high yields, regioselectivity, and enantiomeric excess. The rhodium-catalyzed DYKAT method addresses limitations previously associated with this particular class of aromatic nitrogen nucleophiles.
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, IA 52242, USA.
authors.forename: Jeffrey S
authors.initials: JS
authors.lastname: Arnold
authors.forename: Gregory T
authors.initials: GT
authors.lastname: Cizio
authors.forename: Drew R
authors.initials: DR
authors.lastname: Heitz
authors.forename: Hien M
authors.initials: HM
authors.lastname: Nguyen
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000586:Amination; D000814:Aniline Compounds / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000081:Acetamides; D000814:Aniline Compounds; D062845:Chloroacetates; D012238:Rhodium; C009528:trichloroacetamide; C023650:aniline