Lewis acid-catalyzed cascade radical addition/cyclization for the synthesis of 3-substituted isoindolin-1-one derivatives

Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-o...

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Published inTetrahedron letters Vol. 55; no. 16; pp. 2654 - 2658
Main Authors Zhang, Lianjin, Kim, Jin Bum, Jang, Doo Ok
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.04.2014
Elsevier
Subjects
Cascade
Cascades
Chemistry
Chemistry, Organic
Derivatives
Diastereoselective
Hydrazones
Isoindolinone
L-Proline
Lewis acid
Physical Sciences
Radical addition
Radicals
Science & Technology
Synthesis (chemistry)
Tetrahedrons
Isoindolinone
Lewis acid
Diastereoselective
Radical addition
Cascade
L-Proline
METABOLITES
ASYMMETRIC-SYNTHESIS
CARBON-CARBON BOND
ALLYLATION
CARBOXAMIDES
MAPPICINE
DEOXYGENATION
CONSTRUCTION
OXIME ETHERS
CYCLIZATION
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Summary:Radical addition reactions to 2-formylbenzoate-derived hydrazones in the presence of a Lewis acid were developed. Under the reaction conditions, the resulting products were readily converted into 3-substituted isoindolin-1-one derivatives. Diastereoselective synthesis of 3-substituted isoindolin-1-one derivatives was also established employing L-proline as a chiral auxiliary. The cascade radical addition–cyclization reaction allows direct access to 3-substituted isoindolin-1-one derivatives under tin-free conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.03.023