Nickel-Catalyzed Enantioselective Carbamoyl Iodination: A Surrogate for Carbamoyl Iodides

This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni­(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in u...

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Bibliographic Details
Published in:ACS catalysis 2020-04, Vol.10 (8), p.4780-4785
Main Authors: Marchese, Austin D, Wollenburg, Marco, Mirabi, Bijan, Abel-Snape, Xavier, Whyte, Andrew, Glorius, Frank, Lautens, Mark
Format: Article
Language:English
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Summary:This work reports the enantioselective formal transfer of a carbamoyl iodide across a 1,1-disubstituted styrene using Ni-catalysis. Employing an air-stable Ni­(II) precatalyst and a commercially available chiral ligand ((S)-tBuPHOX), enantioenriched 3,3-disubstituted iodooxindoles were obtained in up to 90% yield and up to 97:3 e.r. This methodology was applied to the total synthesis of (−)-esermethole and (−)-phenserine.
ISSN:2155-5435
2155-5435
DOI:10.1021/acscatal.0c00841