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Iridium-Catalyzed Regio- and Enantioselective Amination
Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.
J. Am. Chem. Soc. 2018;
15 March 2018 (online)
Several π-allyliridium C,O-benzoates are known to act as catalysts for nucleophilic carbonyl allylation. In contrast, the authors report that a π-allyliridium C,O-benzoate modified by SEGPHOS catalyzes the chemo-, regio-, and enantioselective electrophilic aminations of branched allylic acetates bearing linear alkyl groups.
The π-allyliridium C,O-benzoate is commercially available and stable to air, water, and silica-gel chromatography. The authors demonstrated that both nucleophilic and electrophilic allylations proceed with the same iridium catalyst under similar conditions.