Enantioselective Synthesis of Di- and Tri-Arylated All-Carbon Quaternary Stereocenters via Copper-Catalyzed Allylic Arylations with Organolithium Compounds

Abstract

The highly enantioselective copper­(I)/N-heterocyclic carbene (NHC) catalyzed synthesis of di- and triarylated all-carbon quaternary stereocenters via asymmetric allylic arylation (AAAr) with aryl organolithium compounds is demonstrated. The use of readily available or easily accessible aryl organolithium reagents in combination with trisubstituted allyl bromides, in the presence of a copper/NHC catalyst, affords important di- and triarylated all-carbon quaternary stereocenters in good yields and enantioselectivities. This method tolerates a wide range of alkyl and substituted aryl groups in the starting allyl bromides, including less common biaryl moieties, which, in combination with diverse organolithium reagents, delivers a broad scope of products in an operationally straightforward and efficient manner

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    Last time updated on 31/03/2019