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Organocatalyzed Intramolecular Michael Addition of Morita–Baylis–Hillman Adducts of β‐Arylnitroethylenes: An Entry to 3‐Aryl‐4‐nitrocyclohexanones
Author(s) -
Raji Reddy Chada,
Reddy Motatipally Damoder,
Haribabu Kothapalli
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200884
Subject(s) - chemistry , intramolecular force , michael reaction , adduct , baylis–hillman reaction , aryl , organocatalysis , stereochemistry , organic chemistry , catalysis , enantioselective synthesis , alkyl
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.