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
Key words
iridium catalysis - amination - allylic acetates - amphiphilic reactivity
Significance
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.
Comment
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.
