Synfacts 2018; 14(04): 0373
DOI: 10.1055/s-0037-1609359
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium-Catalyzed Regio- and Enantioselective Amination

Hisashi Yamamoto
Takahiro Sawano
Meza AT. Wurm T. Smith L. Kim SW. Zbieg JR. * Stivala CE. * Krische MJ. * Genentech, Inc., South San Francisco and University of Texas, Austin, USA
Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

J. Am. Chem. Soc. 2018;
140: 1275-1279
Further Information

Publication History

Publication Date:
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.