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 with azodicarboxylates took place efficiently at ambient temperature to produce 4-nitro-1-vinyl-1-2,3-benzodiazepine-2,3-dicarboxylates in good to excellent yields with an enantiomeric ratio of up to 95:5.

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http://dx.doi.org/10.1021/acs.joc.9b02693DOI Listing

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