Organocatalyzed Intramolecular Michael Addition of Morita-Baylis-Hillman Adducts of [beta]-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 [beta]-arylnitroethylenes. The strategy involves proline-catalyzed diastereoselective intramolecular Michael addition to obtain 3,4-trans-disubstituted cyclohexanones. This method provides a fac...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-11, Vol.2012 (32), p.6414
Main Authors: Raji Reddy, Chada, Reddy, Motatipally Damoder, Haribabu, Kothapalli
Format: Article
Language:English
Online Access:Get full text
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Summary:The synthesis of 3-aryl-4-nitrocyclohexanones has been achieved from the Morita-Baylis-Hillman adducts of [beta]-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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201200884