Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines
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چکیده
منابع مشابه
Phosphine-catalyzed annulation of ethyl (arylimino)acetates: synthesis of highly functionalized oxoimidazolidines.
This paper describes an unexpected and novel nucleophilic phosphine-catalyzed annulation of ethyl (arylimino)acetates to give polysubstituted oxoimidazolidine derivatives in moderate to good yields from simple and easily available starting materials under mild conditions. In this reaction, the addition of methyl vinyl ketone (MVK) is essential to induce the formation of oxoimidazolidines.
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The first chiral phosphine-catalyzed activation of acrylates for intramolecular formal [2 + 4] reactions with unsaturated imines is described. The catalytic reactions afford N-heterocycles with exceptionally high diastereo- and enantioselectivities. The [2 + 4] products are amenable for further transformations to useful molecules such as chiral piperidines and multicyclic structures.
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A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from readily available enaminones and the cyanomethyl sulfonium bromide salt in the presence of cesium carbonate is developed, and a mechanism involving sequential nucleophilic vinylic substitution (S(N)V), intramolecular nucleophilic cyclization and dealkylation reactions is proposed.
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ژورنال
عنوان ژورنال: Green Synthesis and Catalysis
سال: 2021
ISSN: 2666-5549
DOI: 10.1016/j.gresc.2021.03.001