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

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-(...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 85; no. 2; pp. 612 - 621
Main Authors Ding, Ya-Li, Zhao, Yun-Long, Niu, Shuang-Shuo, Wu, Pei, Cheng, Ying
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.01.2020
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
REDUCTION
CHIRAL RESOLUTION
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Summary: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.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02693