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. 2022 Sep 26;61(39):e202208837.
doi: 10.1002/anie.202208837. Epub 2022 Aug 18.

Diastereo- and Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters via Iridium/Europium Bimetallic Catalysis

Wei Wang  1   2 , Fangqing Zhang  1   2 , Yangbin Liu  2 , Xiaoming Feng  2   3
Affiliations

Diastereo- and Enantioselective Construction of Vicinal All-Carbon Quaternary Stereocenters via Iridium/Europium Bimetallic Catalysis

Wei Wang et al. Angew Chem Int Ed Engl. .

Abstract

The diastereo- and enantioselective construction of vicinal all-carbon quaternary stereocenters is a formidable task. We here report a synergistic bimetallic catalysis via a chiral N,N'-dioxide-europium (Eu) complex and a phosphoramidite-iridium (Ir) catalyst for the asymmetric allylation of oxindole derivatives by using challenging trisubstituted allylic esters. The allylated products bearing vicinal all-carbon quaternary stereocenters were obtained with good diastereoselectivities (up to 20 : 1 dr) and excellent enantioselectivities (up to 99 % ee). Control experiments showed that the complementary diastereomers of the products were not accessible by the change of the stereochemistry of the chiral N,N'-dioxide ligand.

Keywords: Allylic Alkylation; Allylic Electrophiles; Bimetallic Catalysis; N,N′-Dioxide; Quaternary Stereocenters.

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