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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Published in | Journal of organic chemistry Vol. 85; no. 2; pp. 612 - 621 |
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Main Authors | , , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
17.01.2020
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.9b02693 |