Asymmetric Synthesis of Quaternary α-Aryl Stereocentres in Benzofuran-3(2H)-Ones Using Decarboxylative Asymmetric Allylic Alkylation
- PMID: 38752722
- DOI: 10.1002/chem.202401738
Asymmetric Synthesis of Quaternary α-Aryl Stereocentres in Benzofuran-3(2H)-Ones Using Decarboxylative Asymmetric Allylic Alkylation
Abstract
The Pd-catalysed decarboxylative asymmetric allylic alkylation (DAAA) has been applied to the enantioselective synthesis of sterically hindered benzofuran-3(2H)-one-derived α-aryl-β-keto esters employing the (R,R)-ANDEN phenyl Trost ligand. A range of substrates were synthesised, employing previously developed aryllead triacetate methodology to install various aryl groups. The resulting α-aryl-α-allyl benzofuran-3(2H)-one DAAA products were obtained in moderate to high yields and in enantioselectivities of up to 96 % ee, with the best results observed for substrates containing a di-ortho-substitution pattern on the aryl ring as well as naphthyl-containing substrates.
Keywords: allylic alkylation; asymmetric; catalysis; decarboxylation; palladium.
© 2024 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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