Facile domino reactions in the statistically controlled product- and stereoselective synthesis of densely functionalized cis-1,4-cyclohexa-1,4-dienes and trans,trans-trisubstituted-1,2,5,6-tetrahydropyridines

The domino reactions of ethyl 3-oxo-4-(arylsulfonyl)butanoates with aromatic aldehydes in a 2:1 molar ratio in the presence of a catalytic amount of ammonium acetate furnished densely functionalized cyclohexa-1,4-dienes stereoselectively, while the domino reactions of ethyl 3-oxo-4-(arylsulfonyl)but...

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Bibliographic Details
Published inTetrahedron letters Vol. 53; no. 30; pp. 3880 - 3884
Main Authors Sokkan Harikrishnan, Palani, Michael Rajesh, Stephen, Perumal, Subbu
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 25.07.2012
Elsevier
Subjects
1,4-Cyclohexadienes
Ammonium acetate
Aromatic aldehyde
Chemistry
Chemistry, Organic
Domino reaction
Ethyl-3-oxo-4-(arylsulfonyl)butanoates
Physical Sciences
Science & Technology
Tetrahydropyridines
1,4-Cyclohexadienes
Ammonium acetate
Aromatic aldehyde
Ethyl-3-oxo-4-(arylsulfonyl)butanoates
Tetrahydropyridines
Domino reaction
CONCISE
ASYMMETRIC-SYNTHESIS
MECHANISM
MULTICOMPONENT REACTIONS
NITROOLEFINS
CHEMISTRY
INHIBITORS
DERIVATIVES
ALKALOIDS
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Summary:The domino reactions of ethyl 3-oxo-4-(arylsulfonyl)butanoates with aromatic aldehydes in a 2:1 molar ratio in the presence of a catalytic amount of ammonium acetate furnished densely functionalized cyclohexa-1,4-dienes stereoselectively, while the domino reactions of ethyl 3-oxo-4-(arylsulfonyl)butanoates, aromatic aldehydes, and ammonium acetate in a 1:2:2 molar ratio afforded highly functionalized 1,2,5,6-tetrahydropyridines stereoselectively.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.05.071