Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates.
The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et3N·3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et3N·3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the enantioselective construction of secondary allylic fluorides bearing α-linear substituents.
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Qi
Q
Zhang
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
David P
DP
Stockdale
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Jason C
JC
Mixdorf
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Joseph J
JJ
Topczewski
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.
Hien M
HM
Nguyen
D000081:Acetamides / Q000737:chemistry*; D002384:Catalysis; D062845:Chloroacetates / Q000737:chemistry*; D054879:Halogenation; D007495:Iridium / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000081:Acetamides; D062845:Chloroacetates; D007495:Iridium; C009528:trichloroacetamide