Organocatalyzed Intramolecular Michael Addition of Morita-Baylis-Hillman Adducts of β-Arylnitroethylenes: An Entry to 3-Aryl-4-nitrocyclohexanones

The synthesis of 3‐aryl‐4‐nitrocyclohexanones has been achieved from the Morita–Baylis–Hillman adducts of β‐arylnitroethylenes. The strategy involves proline‐catalyzed diastereoselective intramolecular Michael addition to obtain 3,4‐trans‐disubstituted cyclohexanones. This method provides a facile a...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-11, Vol.2012 (32), p.6414-6419
Main Authors: Raji Reddy, Chada, Reddy, Motatipally Damoder, Haribabu, Kothapalli
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Catalysis
Catalysts: preparations and properties
Chemistry
Cyclohexanone
Epibatidine
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Michael addition
Morita-Baylis-Hillman reaction
Nitroalkenes
Organic chemistry
Organocatalysis
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:The synthesis of 3‐aryl‐4‐nitrocyclohexanones has been achieved from the Morita–Baylis–Hillman adducts of β‐arylnitroethylenes. The strategy involves proline‐catalyzed diastereoselective intramolecular Michael addition to obtain 3,4‐trans‐disubstituted cyclohexanones. This method provides a facile access to (±)‐epibatidine analogues. Morita–Baylis–Hillman (MBH) adducts of β‐arylnitroethylenes have been successfully converted into 3‐aryl‐4‐nitrocyclohexanones through an organocatalyzed diastereoselective intramolecular Michael addition. The application of the method towards (±)‐epibatidine and its analogues has also been achieved.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200884