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Asymmetric Synthesis of Multifunctionalized 2,3-Benzodiazepines by a One-Pot N‑heterocyclic Carbene/Chiral Palladium Sequential Catalysis

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journal contribution
posted on 18.12.2019, 02:13 by Ya-Li Ding, Yun-Long Zhao, Shuang-Shuo Niu, Pei Wu, Ying Cheng
We report the first example of the construction of chiral 2,3-benzodiazepine compounds which are of biologic and pharmaceutical relevance by asymmetric catalysis. Catalyzed by a thiazolium-derived carbene and a palladium-chiral bidentate phosphine complex in sequence, one-pot reaction between 1-(2-(2-nitrovinyl)­aryl)­allyl esters 1 with azodicarboxylates 2 took place efficiently at ambient temperature to produce 4-nitro-1-vinyl-1H-2,3-benzodiazepine-2,3-dicarboxylates 5 in good to excellent yields with an enantiomeric ratio of up to 95:5.