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Synfacts 2018; 14(04): 0373
DOI: 10.1055/s-0037-1609359
DOI: 10.1055/s-0037-1609359
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
Iridium-Catalyzed Regio- and Enantioselective Amination
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
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)
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.
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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.
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