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Amphiphilic ?-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.


ABSTRACT: The first examples of amphiphilic reactivity in the context of enantioselective catalysis are described. Commercially available ?-allyliridium C,O-benzoates, which are stable to air, water and SiO2 chromatography, and are well-known to catalyze allyl acetate-mediated carbonyl allylation, are now shown to catalyze highly chemo-, regio- and enantioselective substitutions of branched allylic acetates bearing linear alkyl groups with primary amines.

SUBMITTER: Meza AT 

PROVIDER: S-EPMC6262838 | biostudies-literature | 2018 Jan

REPOSITORIES: biostudies-literature

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Amphiphilic π-Allyliridium C,O-Benzoates Enable Regio- and Enantioselective Amination of Branched Allylic Acetates Bearing Linear Alkyl Groups.

Meza Arismel Tena AT   Wurm Thomas T   Smith Lewis L   Kim Seung Wook SW   Zbieg Jason R JR   Stivala Craig E CE   Krische Michael J MJ  

Journal of the American Chemical Society 20180119 4


The first examples of amphiphilic reactivity in the context of enantioselective catalysis are described. Commercially available π-allyliridium C,O-benzoates, which are stable to air, water and SiO<sub>2</sub> chromatography, and are well-known to catalyze allyl acetate-mediated carbonyl allylation, are now shown to catalyze highly chemo-, regio- and enantioselective substitutions of branched allylic acetates bearing linear alkyl groups with primary amines. ...[more]

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