Base-Catalyzed Domino Double Michael Reactions of 1-Hydroxy-1,4-dien-3-ones and 2-Alkylidenemalononitriles: A Diastereoselective Route to Polysubstituted 3-Alkanoyl-4-hydroxycyclohex-3-enes
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چکیده
منابع مشابه
Uncatalyzed Synthesis of Arylmethylene[bis(5,5-dimethyl-3-hydroxy-2-cyclohexene-1-ones)] in Hot Water by Domino Knoevenagel/Michael Reactions
A simple and ecofriendly method was developed for the synthesis of arylmethylene[bis(5,5- dimethyl-3-hydroxy-2-cyclohexene-1-ones)] from the reaction of 5,5-dimethylcyclohexane- 1,3-dione and aromatic aldehydes in an aqueous media without any catalyst via Knoevenagel condensation followed by rapid Michael addition. No cyclization product was down to convert these enolic forms to xanthene deriva...
متن کاملPhosphine-catalyzed [4 + 2] annulation and vinylogous addition reactions between 1,4-dien-3-ones and 1,1-dicyanoalkenes.
Phosphine-catalyzed [4 + 2] annulation and vinylogous Michael addition reactions between 1,4-dien-3-ones and 1,1-dicyanoalkenes are presented. Under the catalysis of PBu(3) (20 mol %), 1,4-dien-3-ones like styryl ketones with 2-aryl 1,1-dicyanoalkenes as doubly activated alkenes readily undergo a formal [4 + 2] cycloaddition reaction, affording polysubstituted cyclohexanones in satisfactory yie...
متن کاملAsymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea.
The current work reports an organocatalytic strategy for the asymmetric catalysis of chiral benzofuran-2(3H)-ones bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate ...
متن کاملSynthesis, Reactions and Antioxidant Activity of 5-(3', 4'-dihydroxy-tetrahydrofuran-2'-yl)-2-methyl-3-carbohydrazide
In this manuscript, we describe the synthesis of the carbohydrazide 2. Acid-catalyzed condensation with several carbonyl compounds to afford the corresponding carbohydrazide derivatives 3-12. Their acetylation afforded the corresponding acetyl derivatives 13-22. Oxidative cyclization of O-acetyl derivatives 19-22 afforded the corresponding 1,3,4-oxadiazole derivatives 23-2...
متن کاملHighly enantioselective Michael addition reactions of 2-substituted benzofuran-3(2H)-ones to nitroolefins.
A highly enantioselective Michael addition reaction of 2-substituted benzofuran-3(2H)-ones to nitroolefins was promoted by a bifunctional squaramide catalyst. As a result, a number of chiral 2,2'-substituted benzofuran-3-one derivatives, bearing adjacent quaternary-tertiary stereocenters, were efficiently synthesized with excellent enantioselectivities.
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ژورنال
عنوان ژورنال: Synthesis
سال: 2014
ISSN: 0039-7881,1437-210X
DOI: 10.1055/s-0034-1379143