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

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journal contribution
posted on 03.04.2020, 19:36 by Austin D. Marchese, Marco Wollenburg, Bijan Mirabi, Xavier Abel-Snape, Andrew Whyte, Frank Glorius, Mark Lautens
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.

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